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CAS No. : | 271-95-4 | MDL No. : | MFCD00005852 |
Formula : | C7H5NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KTZQTRPPVKQPFO-UHFFFAOYSA-N |
M.W : | 119.12 | Pubchem ID : | 71073 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 34.01 |
TPSA : | 26.03 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.87 cm/s |
Log Po/w (iLOGP) : | 1.72 |
Log Po/w (XLOGP3) : | 1.63 |
Log Po/w (WLOGP) : | 1.83 |
Log Po/w (MLOGP) : | 1.12 |
Log Po/w (SILICOS-IT) : | 2.02 |
Consensus Log Po/w : | 1.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.35 |
Solubility : | 0.538 mg/ml ; 0.00451 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.79 |
Solubility : | 1.94 mg/ml ; 0.0162 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.86 |
Solubility : | 0.163 mg/ml ; 0.00137 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.39 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.5% | at 20℃; for 80 h; | Methyl iodide (20 mL, 320 mmol) was added to a solution of benzooxazole-2-thiol (25.0 g, 165 mmol) taken in dry THF (250 mL) and the reaction mixture was stirred at room temperature for 80 hours, after which it was concentrated to give 2-methylsulfanyl- benzooxazole. EPO <DP n="28"/>Yield : 25.O g (91.50 percent).Mass (EI): 165 (M+); 1H NMR (CDCl3): δ 7.60 (d, IH), 7.42 (d, IH), 7.26 (m, 2H), 2.80 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With chlorosulfonic acid at 0 - 100℃; for 27h; | 10 Synthesis of benzo[d]isoxazole-5-sulfonyl Chloride Synthesis of benzo[d]isoxazole-5-sulfonyl Chloride Into a 50 mL round-bottom flask, was placed CISO3H (2.8 mL). To the mixture was added benzo[d]isoxazole (500 mg, 4.20) dropwise at 0° C. The resulting solution was allowed to react, with stirring, for 27 h while the temperature was maintained at 100° C. in a bath of oil. The reaction progress was monitored by TLC (EtOAc/PE=1:5). The reaction mixture was diluted by CH2Cl2 and poured into 50 mL of H2O/ice cautiously. The aqueous layer was extracted two times with 50 mL of CH2Cl2 and the organic layers combined. The resulting mixture was washed 2 times with 50 mL of water. The mixture was dried over MgSO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 500 mg (48%) of benzo[d]isoxazole-5-sulfonyl chloride as a red solid. 1H NMR (300 MHz, CDCl3, δ) 8.93 (1H, s), 8.54 (1H, s), 8.26 (1H, d), 7.87 (1H, d). ES-MS m/z 287 [M+BnNH-H]- |
48% | With chlorosulfonic acid at 0 - 100℃; for 27h; | 36.3 Benzo[d]isoxazole (4.20 mmol) was added dropwise over 20 min to sulfurochloridic acid (2.8 mL) at 0 °C and the reaction mixture was heated at 100 °C for 27 h. The reaction mixture was diluted by dichloromethane and cautiously poured into ice water (50 mL). The aqueous layer was extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with water (2 x 50 mL), dried (magnesium sulfate), and concentrated to provide benzo[d]isoxazole-5-sulfonyl chloride in 48% yield as a red solid. Data: 1H NMR (CDCl3) δ 8.93 (s, 1H), 8.54 (s, 1H), 8.26 (d, 1H), 7.87 (d, 1H). LC/MS (ES) m/z 287 [M+BnNH-H]-. |
48% | With chlorosulfonic acid at 0 - 100℃; for 27h; | 7.3 3. Synthesis of benzo[d]isoxazole-5-sulfonyl chloride Into a 50 mL round-bottom flask was placed ClSO3H (2.8 mL). To the mixture was added benzo[d]isoxazole (500 mg, 4.20) dropwise at 0 degree C. The resulting solution was allowed to react, with stirring, for 27 hours while the temperature was maintained at 100° C. in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:5). The reaction mixture was diluted by CH2Cl2 and poured into 50 mL of H2O/ice cautiously. The aqueous layer was extracted two times with 50 mL of CH2Cl2 and the organic layers combined. The resulting mixture was washed 2 times with 50 mL of water. The mixture was dried over MgSO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 500 mg (48%) of benzo[d]isoxazole-5-suffonyl chloride as a red solid. 1H NMR(300 MHz, CDCl3) δ 8.93(s, 1H), 8.54(s, 1H), 8.26(d, 1H), 7.87(d, 1H). m/z 287 [M+BnNH-]- |
48% | With chlorosulfonic acid at 0 - 100℃; for 27.3333h; | I.19.3 3. Synthesis of benzo[d]isoxazole-5-sulfonyl chloride; Benzo[d]isoxazole (4.20 mmol) was added dropwise over 20 min to sulfurochloridic acid (2.8 mL) at 0° C. and the reaction mixture was heated at 100° C. for 27 h. The reaction mixture was diluted by dichloromethane and cautiously poured into ice water (50 mL). The aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with water (2×50 mL), dried (magnesium sulfate), and concentrated to provide benzo[d]isoxazole-5-sulfonyl chloride in 48% yield as a red solid. Data: 1H NMR (CDCl3) δ 8.93 (s, 1H), 8.54 (s, 1H), 8.26 (d, 1H), 7.87 (d, 1H). LC/MS (ES) m/z 287 [M+BnNH-H]- |
48% | With chlorosulfonic acid at 0 - 100℃; | 36.3 3. Synthesis of benzo[d]isoxazole-5-sulfonyl chloride.Benzo[d]isoxazole (4.20 mmol) was added dropwise over 20 min to sulfurochloridic acid (2.8 mL) at 0 0C and the reaction mixture was heated at 100 0C for 27 h. The reaction mixture was diluted by dichloromethane and cautiously poured into ice water (50 mL). The aqueous layer was extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with water (2 x 50 mL), dried (magnesium sulfate), and concentrated to provide benzo[d]isoxazole-5-sulfonyl chloride in 48% yield as a red solid. Data: 1H NMR (CDCl3) δ 8.93 (s, IH), 8.54 (s, IH), 8.26 (d, IH), 7.87 (d, IH). LC/MS (ES) m/z 287 [M+BnNH-H]". |
48% | With chlorosulfonic acid at 0 - 100℃; | 3 Benzo[d]isoxazole (4.20 mmol) was added dropwise over 20 min to sulfurochloridic acid (2.8 mL) at 0° C. and the reaction mixture was heated at 100° C. for 27 h. The reaction mixture was diluted by dichloromethane and cautiously poured into ice water (50 mL). The aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with water (2×50 mL), dried (magnesium sulfate), and concentrated to provide benzo[d]isoxazole-5-sulfonyl chloride in 48% yield as a red solid. Data: 1H NMR (CDCl3) δ 8.93 (s, 1H), 8.54 (s, 1H), 8.26 (d, 1H), 7.87 (d, 1H). LC/MS (ES) m/z 287 [M+BnNH-H]- |
48% | With chlorosulfonic acid at 0 - 100℃; for 27.3333h; | 2 3. Synthesis of benzo[d]isoxazole-5-sulfonyl chloride.Benzo[d]isoxazole (4.20 mmol) was added dropwise over 20 min to sulfurochloridic acid (2.8 mL) at 0 0C and the reaction mixture was heated at 100 0C for 27 h. The reaction mixture was diluted by dichloromethane and cautiously poured into ice water (50 mL). The aqueous layer was extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with water (2 x 50 mL), dried (magnesium sulfate), and concentrated to provide benzo[d]isoxazole-5-sulfonyl chloride in 48% yield as a red solid. Data: 1H NMR (CDCl3) δ 8.93 (s, IH), 8.54 (s, IH), 8.26 (d, IH), 7.87 (d, IH). LC/MS (ES) m/z 287 [M+BnNH-H]". |
48% | With chlorosulfonic acid at 0 - 100℃; for 27.33h; | 19.3 3. Benzo[d]isoxazole (4.20 mmol) was added dropwise over 20 min to sulfurochloridic acid (2.8 mL) at 0° C. and the reaction mixture was heated at 100° C. for 27 h. The reaction mixture was diluted by dichloromethane and cautiously poured into ice water (50 mL). The aqueous layer was extracted with dichloromethane (2*50 mL). The combined organic layers were washed with water (2*50 mL), dried (magnesium sulfate), and concentrated to provide benzo[d]isoxazole-5-sulfonyl chloride in 48% yield as a red solid. Data: 1H NMR (CDCl3) δ 8.93 (s, 1H), 8.54 (s, 1H), 8.26 (d, 1H), 7.87 (d, 1H). LC/MS (ES) m/z 287 [M+BnNH-H]- |
48% | With chlorosulfonic acid at 0 - 100℃; for 27h; | 19.3 Into a 50 mL round bottom flask was placed ClSO3H (2.8 mL). To the mixture was added benzo[d]isoxazole (500 mg, 4.20 ) dropwise at 0 0C. The resulting solution was allowed to react, with stirring, for 27 hours while the temperature was maintained at 100 0C in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether = 1:5). The reaction mixture was diluted by CH2Cl2 and poured into 50 mL of H2O /ice cautiously. The aqueous layer was extracted two times with 50 mL of CH2Cl2 and the organic layers combined. The resulting mixture was washed 2 times with 50 mL of water. The mixture was dried over MgSO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 500 mg (48%) of benzo[d]isoxazole-5~ sulfonyl chloride as a red solid.1HNMROOOMHZ, CDC13) δ 8.93(s, IH), 8.54(s, IH), 8.26(d, IH)5 7.87(d, lH).m/z 287 [M+BnNH-H]- |
With chlorosulfonic acid for 27h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With trifluoromethylsulfonic anhydride; In dichloromethane; at 20℃; for 4h;Inert atmosphere; | General procedure: The desired 2-hydroxyaryl aldoxime or ketoxime (2.0 mmol) in 5 mL dry DCM was taken in an oven-dried round-bottom flask. To the reaction mixture was adde ddropwise triflic anhydride (2.0 mmol) in DCM under nitrogen for 15 min. The reaction mixture was stirred at rt and the progress of the reaction was monitored by TLC and GC-MS (Table 1). After completion of reaction, the contents were poured on tocrushed ice (100 mL), neutralized with 10% NaHCO3 solution (20 mL), and extracted with DCM (315 mL). The pure products were obtained by column chromatography with hexane-ethyl acetate mixture (80:20). All the 1,2-benzisoxazole derivatives were characterized by GC-MS, 1H and 13C NMR, and elemental analysis, and the results are compared with authentic samples. |
67% | With 1H-imidazole; trifluoromethylsulfonic anhydride; In dichloromethane; at 20℃; for 4.3h;Inert atmosphere; | General procedure: A mixture of aldoximes (1 mmol) and imidazole (3 mmol) in anhydrous DCM (10-15 mL) was charged into an oven-dried round-bottom flask under nitrogen and the reaction mixture was stirred at r.t. for 20 min, after which triflic anhydride (0.4-1.0 mmol) was added dropwise via syringe under nitrogen, and the reaction mixture was allowed to stir at r.t. for a specific time (Table 1). Progress of the reaction was monitored by TLC and/or by GC-MS. Upon completion, the reaction mixture was quenched with dilute NaHCO3 solution and the product mass was extracted in DCM. The solvent was removed under reduced pressure to yield the crude product which was purified by prep TLC (ethyl acetate-hexane mixture) (80:20), to give the corresponding nitrile (61-88% yield). The structure of the products was confirmed by comparison of their mp or bp, TLC, IR, GC-MS, 1H NMR and 13C NMR data with authentic samples obtained commercially or prepared by literature methods. |
With gallium anchored on polystyrene sulfonate polymer brushes; In acetonitrile; at 90℃; under 3800.26 Torr; for 0.216667h; | General procedure: The dehydration reaction with different oxime substrates (Table 2, entries 1-5) was carried out in a catalytic microreactor at 90 C, 5 atm pressure, with a residence time of 13 min. A substrate concentration of 25 muM was used for all the substrates. The conversions were determined using online UV-vis spectroscopy by following the change in the extinction of a substrate specific wavelength. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With diisopropylamine; In tetrahydrofuran; 5,7-dihydro-3-methyl-6H-pyrrolo<3,2-f>-1,2-benzisoxazol-6-one; | e) 4-[2-[5,7-Dihydro-6H-pyrrolo[4,5-f]-1,2-benzisoxazol-6-one-3-yl]ethyl]-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) ester. The procedure described in Example 7a was followed using the benzisoxazole formed in step d (2.33 g, 12.4 mmol), 1M LDA (40.9 mL, 40.9 mmol), and 4-iodomethyl-1-piperidine-carboxylic acid, 1-(1,1-dimethylethyl) ester (4.42 g, 13.6 mmol) in dry THF (500 mL), except that after addition of reagents, the mixture was stirred at -78 C. for 4 hours. Purification by chromatography (20%?30% EtOAc/CH2 Cl2) gave recovered starting material (0.210 g, 9%) and the title compound (2.75 g, 58%) as an off-white solid. 1 H-NMR (CDCl3) delta8.48 (s, 1H), 7.44 (s, 1H), 7.03 (s, 1H), 4.08-4.14 (m, 2H), 3.63 (s, 2H), 2.97 (t, 2H, J=7.8 Hz), 2.69 (br t, 2H, J=12.8 Hz), 1.74-1.84 (m, 4H), 1.46-1.55 (m, 1H), 1.46 (s, 9H), 1.18 (ddd, 2H, J=24.4 Hz, J=12.1 Hz, J=4.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With diisopropylamine; In tetrahydrofuran; 5,6,8-Trihydro-7H-isoxazolo[4,5-g]quinolin-7-one; | e 4-[2-[5,6,8-Trihydro-7H-isoxazolo[4,5-g]quinolin-7-one-3-yl]ethyl]-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl)ester The procedure described in Example 7a was followed with the benzisoxazole obtained in step d (0.47 g, 2.3 mmol), 1M LDA (8.1 mL, 8.1 mmol), and 4-iodomethyl-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) ester (0.75 g, 2.3 mmol) in dry THF (150 mL), except that after addition of reagents, the mixture was stirred at -78 C. for 3.5 hours. An additional reaction was benzisoxazole obtained in step d (0.206 g, 1.02 mmol) was carried out in the same manner. Crude product from both reactions was combined and purification by chromatography (EtOAc) gave the title compound (0.72 g, 54% as a white solid. 1 H-NMR (DMSO-d6) delta10.4 (s, 1H), 7.67 (s, 1H), 7.02 (s, 1H), 3.93 (brd, 2H, J=13.4 Hz), 2.89-3.31 (m, 4H), 2.57-2.75 (brm, 2H), 2.49-2.53 (m, 2H), 1.64-1.72 (m, 4H), 1.38 (s, 9H), 1.36-1.50 (m, 1H), 1.01-1.16 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With diisopropylamine; In tetrahydrofuran; 6,8-dihydro-3-methyl-7H-pyrrolo<2,3-g>-1,2-benzisoxazol-7-one; | e 4-[2-[6,8-Dihydro-7H-pyrrolo[5,4-g]-1,2-benzisoxazol-7-one-3-yl]ethyl]-1-piperidinecarboxylic acid 1-(1,1-dimethylethyl)ester The procedure described in Example 7a was followed with the benzisoxazole obtained in step d (0.040 g, 0.213 mmol), 1M LDA (0.85 mL, 0.85 mmol), and 4-iodomethyl-1-piperidine-carboxylic acid, 1-(1,1-dimethylethyl)ester (0.078 g, 1.234 mmol) in dry THF (20 mL), except that after addition of reagents, the mixture was stirred at -78 C. for 4 hours. Purification by chromatography (25?45% EtOAc-CH2 Cl2) gave the title compound (0.042 g, 51%) as a pale yellow solid. 1 -NMR (CDCl3) delta8.85 (s, 1H), 7.53 (d, 1H, J=8.1 Hz), 6.95 (d, 1H, J=8.3 Hz), 4.08-4.14 (m, 2H), 3.78 (s, 2H), 2.99 (t, 2H, J=7.8 Hz), 2.68 (brt, 2H, J=12.1 Hz), 1.73-1.84 (m, 4H), 1.46-1.60 (m, 1H), 1.46 (s, 9H), 1.17 (ddd, 2H, J=23.2 Hz, J=12.1 Hz, J=4.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisopropylamine; In tetrahydrofuran; 5,7-dihydro-3-methyl-6H-pyrrolo<2,3-f>-1,2-benzisoxazol-6-one; | e 4-[2-[5,7-Dihydro-6H-pyrrolo[5,4-f]-1,2-benzisoxazol-6-one-3-yl]ethyl]-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl)ester The procedure described in Example 7a was followed with the benzisoxazole obtained in step d (0.152 g, 0.808 mmol), 1M LDA (3.2 mL, 3.2 mmol), and 4-iodomethyl-1-piperidine-carboxylic acid, 1-(1,1-dimethylethyl) ester (0.315 g, 0.970 mmol) in dry THF (30 mL), except that after addition of reagents, the mixture was stirred at -78 C. for 4.5 hours. Purification by chromatography (50% EtOAc-CH2 Cl2) gave an inseparable mixture (0.153 g, 1.6:1) of starting material and the title compound, respectively, as a pale yellow soft solid. In a separate experiment, a better ratio (starting material/title compound?1:3) was observed. 1 H-NMR (CDCl3) delta9.84 (s, 1H), 7.45 (s, 1H), 7.05 (s, 1H), 4.05-4.15 (m, 2H), 3.69 (s, 2H), 2.96 (t, 2H, J=7.8 Hz), 2.68 (brt, 2H, J=11.8 Hz), 1.72-1.82 (m, 4H), 1.45 (s, 9H), 1.43-1.53 (m, 1H), 1.15 (ddd, 2H, J=23.6 Hz, J=12.1 Hz, J=4.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 4℃; for 5h; | 10 Synthesis of benzo[d]isoxazole Synthesis of benzo[d]isoxazole Into a 1 L 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (E)-2-hydroxybenzaldehyde oxime (3 g, 21.90 mmol) in THF (300 mL). To the mixture was added PPh3 (6.024 g, 22.99 mmol), while cooling to a temperature of 4° C. This was followed by the addition of a solution of DEAD (4 g, 22.99 mmol) in THF (150 mL), while cooling to a temperature of 4° C. over a time period of 4 h. The resulting solution was allowed to react, with stirring, for 1 h while the temperature was maintained at 4° C. in a bath of H2O/ice. The reaction progress was monitored by TLC (EtOAc/PE=1:2). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a 1:100 EtOAc/PE solvent system. This resulted in 1.8 g (66%) of benzo[d]isoxazole as a yellow oil. |
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 5h; | 36.2 A solution of DEAD (23.0 mmol) in tetrahydrofuran (150 mL) was added over a period of 4 h to a solution of (E)-2-hydroxybenzaldehyde oxime (21.9 mmol) and triphenylphosphine (23.0 mmol) in tetrahydrofuran (300 mL) at 0 °C. The reaction mixture was maintained at 0 °C for an additional 60 min and was concentrated. The residue was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to provide benzo[d]isoxazole in 66% yield as yellow oil. |
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 4℃; for 5h; | 7.2 2. Synthesis of benzo[d]isoxazole Into a 1 L 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (E)-2-hydroxybenzaldehyde oxime (3 g, 21.90 mmol) in Tri (300 mL). To the mixture was added PPh3 (6.024 g, 22.99 mmol), while cooling to a temperature of 4° C. This was followed by the addition of a solution of DEAD (4 g, 22.99 mmol) in THF (150 mL), while cooling to a temperature of 4° C. over a time period of 4 hours. The resulting solution was allowed to react with stirring, for 1 hour while the temperature was maintained at 4° C. in a bath of H2O/ice. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a 1:100 ethyl acetate/petroleum ether solvent system. This resulted in 1.8 g (66%) of benzo[d]isoxazole as yellow oil. |
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 5h; | I.19.2 2. Synthesis of benzo[d]isoxazole; A solution of DEAD (23.0 mmol) in tetrahydrofuran (150 mL) was added over a period of 4 h to a solution of (E)-2-hydroxybenzaldehyde oxime (21.9 mmol) and triphenylphosphine (23.0 mmol) in tetrahydrofuran (300 mL) at 0° C. The reaction mixture was maintained at 0° C. for an additional 60 min and was concentrated. The residue was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to provide benzo[d]isoxazole in 66% yield as yellow oil. |
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 5h; | 36.2 2. Synthesis of benzo|"d"|isoxazole.A solution of DEAD (23.0 mmol) in tetrahydrofuran (150 mL) was added over a period of 4 h to a solution of (E)-2-hydroxybenzaldehyde oxime (21.9 mmol) and triphenylphosphine (23.0 mmol) in tetrahydrofuran (300 mL) at 0 0C. The reaction mixture was maintained at 0 0C for an additional 60 min and was concentrated. The residue was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to provide benzo[d]isoxazole in 66% yield as yellow oil. |
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 5h; | 2 A solution of DEAD (23.0 mmol) in tetrahydrofuran (150 mL) was added over a period of 4 h to a solution of (E)-2-hydroxybenzaldehyde oxime (21.9 mmol) and triphenylphosphine (23.0 mmol) in tetrahydrofuran (300 mL) at 0° C. The reaction mixture was maintained at 0° C. for an additional 60 min and was concentrated. The residue was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to provide benzo[d]isoxazole in 66% yield as yellow oil. |
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; | 2 2. Synthesis of benzofd"|isoxazole.A solution of DEAD (23.0 mmol) in tetrahydrofuran (150 mL) was added over a period of 4 h to a solution of (E)-2-hydroxybenzaldehyde oxime (21.9 mmol) and triphenylphosphine (23.0 mmol) in tetrahydrofuran (300 mL) at 0 0C. The reaction mixture was maintained at 0 0C for an additional 60 min and was concentrated. The residue was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to provide benzo[d]isoxazole in 66% yield as yellow oil. |
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 5h; | 19.2 2. A solution of DEAD (23.0 mmol) in tetrahydrofuran (150 mL) was added over a period of 4 h to a solution of (E)-2-hydroxybenzaldehyde oxime (21.9 mmol) and triphenylphosphine (23.0 mmol) in tetrahydrofuran (300 mL) at 0° C. The reaction mixture was maintained at 0° C. for an additional 60 min and was concentrated. The residue was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to provide benzo[d]isoxazole in 66% yield as yellow oil. |
66% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 4℃; for 5h; | 19.2 Into a 1 L 3 -necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (E)-2-hydroxybenzaldehyde oxime (3 g, 21.90 mmol) in tetrahydrofuran (300 mL). To the mixture was added PPh3 (6.024 g, 22.99 mmol), while cooling to a temperature of 4 0C. This was followed by the addition of a solution of DEAD (4 g, 22.99 mmol) in tetrahydrofuran (150 mL), while cooling to a temperature of 4 0C over a time period of 4 hours. The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at 4 0C in a bath of H2O /ice. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether = 1:2). The mixture was concentrated by evaporation under vacuum using a rotary evaporator.The residue was purified by eluting through a column with a 1:100 ethyl acetate/petroleum ether solvent system. This resulted in 1.8 g (66%) of benzo[d]isoxazole as yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.50% | In tetrahydrofuran; at 20℃; for 80h; | Methyl iodide (20 mL, 320 mmol) was added to a solution of benzooxazole-2-thiol (25.0 g, 165 mmol) taken in dry THF (250 mL) and the reaction mixture was stirred at room temperature for 80 hours, after which it was concentrated to give 2-methylsulfanyl- benzooxazole. EPO <DP n="28"/>Yield : 25.O g (91.50 %).Mass (EI): 165 (M+); 1H NMR (CDCl3): delta 7.60 (d, IH), 7.42 (d, IH), 7.26 (m, 2H), 2.80 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With N-Bromosuccinimide In N,N-dimethyl-formamide at -15 - 60℃; for 6h; Inert atmosphere; Sealed tube; | 24.1 the preparation of compound 24-2 To a solution of NBS (2.16 g, 12 mmol) in DMF (6.0 mL) was added a solution of compound 24-1 (0.71 g, 6.0 mmol) in DMF (6.0 mL) dropwise in the dark at -15 °C. At the end of the addition, the mixture was stirred at rt for 1.0 hr and at 60 °C for another 5.0 hrs. After the reaction was completed, the mixture was poured into the mixed solvents of ice water (50 mL) and diethyl ether (60 mL). The organic layer was separated, washed several times with water to neutral H, dried over anhydrous Na2SC>4 and concentrated in vacuo to give the title compound (1.07 g, 65%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 275.5 [M+H]+; and NMR (400 MHz, CDC13) δ (ppm): 9.02 (d, 1H), 7.53, 7.51 (s, s, 1H), 7.34, 7.32 (d, d, 1H). |
65% | With N-Bromosuccinimide In N,N-dimethyl-formamide at -15 - 60℃; for 5h; Darkness; | 27.1 the preparation of compound 27-2 A solution of -bromosuccinimide (NBS) (2.16 g, 12 mmol) in anhydrous DMF (6.0 mL) was slowly added dropwise in the dark to a solution of compound 27-1 (0.72 g, 6.0 mmol) in anhydrous DMF (6.0 mL) at-15°C. At the end of the addition, the mixture was stirred at room temperature for 1.0 hr and then at 60°C for another 5.0 hrs. After the reaction was completed, the mixture was poured into 50 mL of ice water and 60.0 mL of ethyl ether. The organic layer was separated, washed several times with water to neutral pH. and dried with anhydrous Na2S04. The solvent was evaporated to give an oily liquid (1.07 g. 65%). The compound was characterized by the following spectroscopic data:MS (ESI, pos.ion) mlz: 275.5 [M+H] ; and NMR (400 MHz, CDCL) (ppm): 9.02 (d.1H).7.53.7.51 (s, s.1 H), 7.34.7.32 (d. d.1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In 1,2-dichloro-ethane at 25℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With zinc trifluoromethanesulfonate In 1,2-dichloro-ethane at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In 1,2-dichloro-ethane at 25℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In 1,2-dichloro-ethane at 25℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In 1,2-dichloro-ethane at 25℃; for 11h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In 1,2-dichloro-ethane at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In 1,2-dichloro-ethane at 25℃; for 11h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In 1,2-dichloro-ethane at 25℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In 1,2-dichloro-ethane at 25℃; for 11h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In 1,2-dichloro-ethane at 25℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In 1,2-dichloro-ethane at 25℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane at 60℃; Inert atmosphere; Schlenk technique; | 1; 17; 18; 19 Embodiment 1: In a 25 mL Schlenk reaction tube equipped with a magnetic stir bar,Adding catalyst Rh2(esp)2 (0.01 mmol, 0.02 equiv.),N-(3-diazo-1-methylindoline-2-ylidene)-4-methylbenzenesulfonamide(1.5 mmol, 3.0 equiv), benzoxazole (0.5 mmol, 1.0 equiv.)And dichloromethane (5 mL), nitrogen protection. The reaction solution was placed in an oil bath at 60 ° C for about 2 to 4 hours, and the reaction was completed by TLC.The reaction solution was then cooled to room temperature.In the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel.The obtained filtrate is separated by flash column chromatography to obtain a pure product.4-methyl-N-(1'-methylspiro[benzo[e][1,3]oxazine-2,3'-carboline]-2'-methylene)benzenesulfonamide.Yield: 74%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane at 60℃; Inert atmosphere; Schlenk technique; | 8 Embodiment 8: In a 25 mL Schlenk reaction tube equipped with a magnetic stir bar,Adding catalyst Rh2(esp)2 (0.01 mmol, 0.02 equiv.),N-(3-diazo-1-methylindolino-2-ethylidene)-4-methoxybenzenesulfonamide(1.5 mmol, 3.0 equiv), benzoxazole (0.5 mmol, 1.0 equiv.)And dichloromethane (5 mL), nitrogen protection. The reaction solution was placed in an oil bath at 60 ° C for about 2 to 4 hours, and the reaction was completed by TLC, and then the reaction mixture was cooled to room temperature.In the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel.The obtained filtrate is separated by flash column chromatography to obtain a pure product.4-methoxy-N-(1'-methylspiro[benzo[e][1,3]oxazine-2,3'-carboline]-2'-methylene)benzenesulfonamide.Yield: 50%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane at 60℃; Inert atmosphere; Schlenk technique; | 10 Embodiment 10 In a 25 mL Schlenk reaction tube equipped with a magnetic stir bar,Adding catalyst Rh2(esp)2 (0.01 mmol, 0.02 equiv.),N-(1-butyl-3-diazonium-2-ethylidene)-4-methylbenzenesulfonamide(1.5 mmol, 3.0 equiv), benzoxazole (0.5 mmol, 1.0 equiv.)And dichloromethane (5 mL), nitrogen protection. The reaction solution was placed in an oil bath at 60 ° C for about 2 to 4 hours, and the reaction was completed by TLC, and then the reaction mixture was cooled to room temperature.In the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel.The obtained filtrate is separated by flash column chromatography to obtain a pure product.N-(1'-butylspiro[benzo[e][1,3]oxazine-2,3'-carboline]-2'-methylene)-4-methylbenzenesulfonamide.Yield: 65%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane at 60℃; Inert atmosphere; Schlenk technique; | 11 Embodiment 11: In a 25 mL Schlenk reaction tube equipped with a magnetic stir bar,Adding catalyst Rh2(esp)2 (0.01 mmol, 0.02 equiv.),N-(3-diazo-1-ethyldihydroindol-2-ylidene)-4-methylbenzenesulfonamide(1.5 mmol, 3.0 equiv), benzoxazole (0.5 mmol, 1.0 equiv.)And dichloromethane (5 mL), nitrogen protection. The reaction solution was placed in an oil bath at 60 ° C for about 2 to 4 hours, and the reaction was completed by TLC, and then the reaction mixture was cooled to room temperature.In the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel.The obtained filtrate is separated by flash column chromatography to obtain a pure product.N-(1'-Ethylspiro[benzo[e][1,3]oxazine-2,3'-carboline]-2'-methylene)-4-methylbenzenesulfonamide. Yield: 45%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane at 60℃; Inert atmosphere; Schlenk technique; | 12 Embodiment 12 In a 25 mL Schlenk reaction tube equipped with a magnetic stir bar,Adding catalyst Rh2(esp)2 (0.01 mmol, 0.02 equiv.),N-(1-allyl-3-azin-2-yl)-4-methylbenzenesulfonamide (1.5 mmol, 3.0 equiv),Benzisazole (0.5 mmol, 1.0 equiv.) and dichloromethane (5 mL) were protected with nitrogen.The reaction solution was placed in an oil bath at 60 ° C for about 2 to 4 hours, and the reaction was completed by TLC.The reaction solution was then cooled to room temperature. In the post-treatment, the catalyst is first removed by suction filtration through a sand core funnel equipped with silica gel, and the obtained filtrate is separated into a pure product by flash column chromatography.N-(1'-Allyl spiro[benzo[e][1,3]oxazine-2,3'-carboline]-2'-methylene)-4-methylbenzenesulfonamide. Yield: 60%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane at 60℃; Inert atmosphere; Schlenk technique; | 14 Embodiment 14 In a 25 mL Schlenk reaction tube equipped with a magnetic stir bar,Adding catalyst Rh2(esp)2 (0.01 mmol, 0.02 equiv.),N-(3-Azo-5-methoxy-1-methylindan-2-yl)-4-methylbenzenesulfonamide(1.5 mmol, 3.0 equiv), benzoxazole (0.5 mmol, 1.0 equiv.)And dichloromethane (5 mL), nitrogen protection. The reaction solution was placed in an oil bath at 60 ° C for about 2 to 4 hours, and the reaction was completed by TLC, and then the reaction mixture was cooled to room temperature.In the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel.The obtained filtrate is separated by flash column chromatography to obtain a pure product.N-(5'-methoxy-1'-methylspiro[benzo[e][1,3]oxazine-2,3'-carboline]-2'-methylene)-4- Methylbenzenesulfonamide. Yield: 45%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane at 60℃; Inert atmosphere; Schlenk technique; | 16 Embodiment 16 In a 25 mL Schlenk reaction tube equipped with a magnetic stir bar,Adding catalyst Rh2(esp)2 (0.01 mmol, 0.02 equiv.),N-(3-diazo-1,7-dimethyl porphyrin-2-ethylene)-4-methylbenzenesulfonamide(1.5 mmol, 3.0 equiv), benzoxazole (0.5 mmol, 1.0 equiv.)And dichloromethane (5 mL), nitrogen protection. The reaction solution was placed in an oil bath at 60 ° C for about 2 to 4 hours, and the reaction was completed by TLC, and then the reaction mixture was cooled to room temperature.In the post-treatment, the catalyst is removed by suction filtration through a sand core funnel equipped with silica gel.The obtained filtrate is separated by flash column chromatography to obtain a pure product.N-(1',7'-dimethylspiro[benzo[e][1,3]oxazine-2,3'-carboline]-2'-methylene)-4-methylbenzene Sulfonamide. Yield: 58% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
75% | With sodium hydroxide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
83% | With sodium hydroxide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium hydroxide at 20℃; for 1h; | |
57% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
65% | With sodium hydroxide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 85% 2: 15% | With sodium carbonate at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
1: 16% 2: 20% | With sodium carbonate In 2,2,2-trifluoroethanol at 20℃; for 0.5h; regioselective reaction; | 2. Typical procedure of cyclization A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with benzo[d]isoxazole (0.1 mmol), N-(benzyloxy)-2-bromo-2-methylpropanamide (0.2 mmol), Na2CO3 (0.4 mmol) in HFIP (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. When the reaction was completed (as judged by thin layer chromatographic analysis), the mixture was diluted with ethyl acetate. The crude material was then filtered through Celite and thoroughly washed with ethyl acetate. The filtrate was then concentrated under rotary evaporation and then purified by column chromatography on silica gel (Petroleum/EtOAc = 20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With (triphenylphosphine)gold(I) chloride; silver(I) acetate; lithium carbonate In toluene at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 2. General procedure for the preparation of (Z)-3a General procedure: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol)at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a(0.75 mmol) dissolved in toluene (1.0 mL) was added via a syringe. The reaction wasraised to 80 oC for about 4-6 h. After completion of the reaction as indicated by TLC,the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0mL), and extracted. The combined organic phase was washed with brine, dried overNa2SO4, and concentrated to give the crude residue, which was purified by silicacolumn chromatography (elute: petroleum ether/ethyl acetate = 20/1, v/v) to give thedesired product 3a as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With caesium carbonate; copper(I) bromide In dichloromethane at 110℃; for 6h; Schlenk technique; | 1; 9-11 The preparation method is: adding benzisoxazole (0.2mmol, 23.8mg), ammonium salt (0.24mmol, 61.7mg), cuprous bromide (0.02mmol, 2.9mg) and cesium carbonate (0.5mmol, 162.9mg) Into a 25ml Schlenk tube, under reduced pressure, the reaction tube was replaced with oxygen three times. Dichloromethane (2ml) was added and stirred at 110°C for 6 hours. After the reaction is over, 200-300 mesh column chromatography silica gel is added, and the solvent is distilled off under reduced pressure. The crude product is subjected to silica gel column chromatography and mixed with petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 20:1). Liquid elution, tracking detection by TLC elution, collecting the eluent containing the target product, combining the eluent of the target product, and evaporating and concentrating to obtain 2,3-diacylquinoline compounds with a yield rate of 58%. The substance is a yellow-brown solid with a melting point of 120.2-122.5°C. |
Tags: 271-95-4 synthesis path| 271-95-4 SDS| 271-95-4 COA| 271-95-4 purity| 271-95-4 application| 271-95-4 NMR| 271-95-4 COA| 271-95-4 structure
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Code | Phrase |
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H316 | Causes mild skin irritation |
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H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
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Environmental hazards | |
Code | Phrase |
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H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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