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Limited Quantity
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Structure of 135-19-3 * Storage: {[proInfo.prStorage]}
* 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.
Reference:
[1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 10, p. 859 - 862
2
[ 133-89-1 ]
[ 135-19-3 ]
[ 6044-30-0 ]
Yield
Reaction Conditions
Operation in experiment
89%
With Aloe*arborescens*glycosyltransferase*GT3 In dimethyl sulfoxide at 30℃; for 12 h; Enzymatic reaction
General procedure: Generally 30-50 μmol of aglycon was solved in 0.5 mL DMSO and diluted with buffer solution (50 mM Tris HCl, pH 7.4, 25 mL total volume). UDP-Glc (60100 μmol) was added along with 50 mL of crude enzyme of AaGT3, extracted from 3 g in wet induced E. coli cells with pET28a-AaGT3. The reactions were performed at 30 °C for up to 12 h, followed by adding 5 × 100 mL of ethyl acetate to extract 5 times. The organic phase was evaporated to dryness under reduced pressure, and the residue was dissolved in 1.5 mL of methanol and purified by reverse-phase semi-preparative HPLC. The obtained products were analyzed by MS and NMR.
Reference:
[1] Journal of Organic Chemistry, 1991, vol. 56, # 21, p. 6148 - 6151
8
[ 141-75-3 ]
[ 135-19-3 ]
[ 5856-33-7 ]
Reference:
[1] Organic Letters, 2008, vol. 10, # 21, p. 4951 - 4953
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 362
[3] Journal fuer Praktische Chemie (Leipzig), 1933, vol. <2> 137, p. 47,51
[4] Journal of the Chemical Society, 1965, p. 168 - 175
9
[ 123-20-6 ]
[ 135-19-3 ]
[ 5856-33-7 ]
Yield
Reaction Conditions
Operation in experiment
106.9 mg
With sodium carbonate In acetonitrile at 120℃; for 24 h; Schlenk technique
General procedure: A mixture of phenol 1 (0.50 mmol), Na2CO3 (10.6 mg, 0.10mmol, 20 molpercent), and alkenyl carboxylate (2.0 mmol, 4.0 equiv)in MeCN (3 mL) was added to a Schlenk flask (25 mL) and stirredat r.t. The mixture was stirred at 120 °C until the reaction wasfinished. Then, the solvent was evaporated under reduced pressureand the residue was purified by column chromatography(petroleum ether/ethyl acetate 20:1 to 10:1) to afford theproduct 3.
Reference:
[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 36, p. 8452 - 8456
22
[ 135-19-3 ]
[ 947-65-9 ]
Reference:
[1] Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17352 - 17353
23
[ 135-19-3 ]
[ 5773-80-8 ]
Reference:
[1] Patent: CN106542971, 2017, A,
24
[ 135-19-3 ]
[ 1779-11-9 ]
Reference:
[1] Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17352 - 17353
25
[ 109-65-9 ]
[ 135-19-3 ]
[ 10484-56-7 ]
Yield
Reaction Conditions
Operation in experiment
95%
With potassium carbonate In acetonitrile at 125℃; for 1 h; Microwave irradiation
General procedure: A mixture of 0.14 g (1.0 mmol) of 1- and 2-naphthol (1)and (6), in most cases 1.0 mmol of alkali carbonate (0.14 g of K2CO3 or 0.33 g of Cs2CO3), in certain cases 11.4 mg(0.05 mmol) of TEBAC and 1.2 mmol of alkyl halide (0.14ml of benzyl bromide, 0.10 ml of ethyl iodide, 0.12 mol ofbutyl bromide or 0.11 ml of i-propyl bromide) in a closedvial was irradiated (20–30 W) in a CEM Discover [300 W]MW reactor at 125 °C for the appropriate time. The reactionmixture was taken up in 25 ml of ethyl acetate and the suspensionwas filtered. Evaporation of the volatile componentsprovided the crude product that was passed through a thin(ca. 2–3 cm) layer of silica gel using ethyl acetate as theeluant to give an oil that was analysed by GC–MS or GC.Similar reactions were carried out in 3 ml of MeCN asthe solvent. The work-up was similar to that described forthe solventless alkylations above, but in this case, ethyl acetatedid not have to be added.The major components of the above reactions, such ascompounds 2, 7, 8, 10a-c and 13a,b were obtained in a pureform by repeated chromatography.Control experiments were performed with benzyl bromidein a similar way under conventional heating.
Reference:
[1] Chemical Communications, 1998, # 20, p. 2245 - 2246
[2] Letters in Organic Chemistry, 2013, vol. 10, # 5, p. 330 - 336
26
[ 135-19-3 ]
[ 71-36-3 ]
[ 10484-56-7 ]
Reference:
[1] Green Chemistry, 2011, vol. 13, # 9, p. 2482 - 2488
[2] Zhurnal Obshchei Khimii, 1951, vol. 21, p. 584,588; engl. Ausg. S. 647, 650
Reference:
[1] Green Chemistry, 2015, vol. 17, # 3, p. 1408 - 1413
30
[ 135-19-3 ]
[ 2033-42-3 ]
Yield
Reaction Conditions
Operation in experiment
74%
With sulfuric acid; dihydrogen peroxide; potassium iodide In methanol at 0 - 20℃;
To a stirred solution of 2-naphthol (1.0g, 6.9 mmol) and conc. H2SO4 (0.54 mL 10.4 mmol) in CH3OH (20 mL) at 0 °Cwas added KI (1.27 g, 7.62 mmol) and 30percent H2O2 (1.56 mL, 13.9 mmol). The mixture was stirred overnight at room temperature, and then poured into CH3Cl. The mixture was washed with saturated aq. NaHSO3,with water, and dried over MgSO4, concentrated in vacuo. The crude product was purified by flash column chromatography using hexane and EtOAc to give 1-iodo-2-naphthol as light yellow solid (1.40 g, 74percent), 1H NMR (300 MHz,CDCl3) d 7.91 (d, J = 8.6 Hz, 1H), 7.73–7.70 (m, 2H), 7.53 (dd, J = 7.1, 8.2 Hz, 1H), 7.36 (dd, J= 7.0, 8.1 Hz, 1H), 7.25-7.23 (m, peak merged with CDCl3, 1H), 5.79(s, 1H); 13C NMR (75 MHz, CDCl3) d 153.7, 134.7, 130.6, 130.2, 129.6, 128.3,128.1, 124.1, 116.4, 86.2; GC-MS m/z 270, 272 (M+).
Reference:
[1] Chemistry Letters, 2011, vol. 40, # 12, p. 1343 - 1345
[2] Journal of Organic Chemistry, 1985, vol. 50, # 25, p. 5384 - 5387
[3] Synthesis, 2010, # 9, p. 1467 - 1472
[4] Synthesis, 2004, # 11, p. 1869 - 1873
[5] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2664 - 2667
[6] Journal of Chemical Research, 2006, # 9, p. 575 - 576
[7] Journal of Chemical Research, 2004, # 4, p. 294 - 295
[8] Chemistry - A European Journal, 2011, vol. 17, # 30, p. 8452 - 8461
[9] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889
[10] Journal of the American Chemical Society, 2018, vol. 140, # 23, p. 7056 - 7060
[11] Canadian Journal of Chemistry, 1987, vol. 65, p. 2019 - 2023
[12] Synthetic Communications, 2006, vol. 36, # 13, p. 1915 - 1917
[13] Patent: JP2004/513951, 2004, A, . Location in patent: Page 21
[14] Angewandte Chemie - International Edition, 2013, vol. 52, # 13, p. 3668 - 3671[15] Angew. Chem., 2013, vol. 52, # 13, p. 3756 - 3759,4
[16] Tetrahedron, 2008, vol. 64, # 1, p. 234 - 239
[17] Tetrahedron Letters, 2008, vol. 49, # 5, p. 893 - 895
[18] Organic Letters, 2008, vol. 10, # 7, p. 1333 - 1336
[19] Journal of Organic Chemistry, 2009, vol. 74, # 16, p. 6287 - 6290
[20] Synthetic Communications, 2004, vol. 34, # 15, p. 2829 - 2833
[21] Helvetica Chimica Acta, 2010, vol. 93, # 2, p. 345 - 349
[22] Synthetic Communications, 2010, vol. 40, # 23, p. 3506 - 3513
[23] Synthetic Communications, 2008, vol. 38, # 17, p. 2881 - 2888
[24] Chinese Chemical Letters, 2011, vol. 22, # 12, p. 1427 - 1430
[25] Tetrahedron Letters, 2003, vol. 44, # 27, p. 5099 - 5101
[26] Tetrahedron Letters, 2014, vol. 55, # 22, p. 3355 - 3357
[27] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 3, p. 258 - 261
[28] Heterocycles, 2015, vol. 90, # 2, p. 919 - 927
[29] Tetrahedron Letters, 1985, vol. 26, # 17, p. 2043 - 2046
[30] Synthesis, 2008, # 15, p. 2327 - 2332
[31] Journal of the Chemical Society, 1885, vol. 47, p. 523[32] Journal of the Chemical Society, 1895, vol. 67, p. 912
[33] Gazzetta Chimica Italiana, 1890, vol. 20, p. 105
[34] Journal of the Chemical Society, 1927, p. 3164
[35] Journal of the Indian Chemical Society, 1933, vol. 10, p. 595,597
[36] Pharmaceutica Acta Helvetiae, 1946, vol. 21, p. 225,227
[37] Austral. J. scient. Res., 1948, vol. <A> 2, p. 246,247
[38] Austral. J. scient. Res., 1948, vol. <A> 2, p. 246,247
[39] Zhurnal Obshchei Khimii, 1954, vol. 24, p. 1265,1270; engl. Ausg. S. 1251, 1254
[40] Journal of the Indian Chemical Society, 1933, vol. 10, p. 595,597
[41] Pharmaceutica Acta Helvetiae, 1946, vol. 21, p. 225,227
[42] Journal of Organic Chemistry, 1990, vol. 55, # 18, p. 5287 - 5291
[43] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, p. 255 - 260
[44] Synthetic Communications, 2004, vol. 34, # 19, p. 3579 - 3585
[45] Synlett, 2005, # 18, p. 2837 - 2842
[46] Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7485 - 7487
[47] Patent: WO2007/27917, 2007, A2, . Location in patent: Page/Page column 26-27
[48] Catalysis Letters, 2010, vol. 137, # 3-4, p. 190 - 201
[49] New Journal of Chemistry, 2012, vol. 36, # 3, p. 597 - 602
31
[ 530-93-8 ]
[ 2033-42-3 ]
[ 135-19-3 ]
Reference:
[1] Green Chemistry, 2016, vol. 18, # 24, p. 6462 - 6467
32
[ 7553-56-2 ]
[ 127-09-3 ]
[ 546-67-8 ]
[ 64-19-7 ]
[ 135-19-3 ]
[ 2033-42-3 ]
Reference:
[1] Journal of the Chemical Society, 1885, vol. 47, p. 523[2] Journal of the Chemical Society, 1895, vol. 67, p. 912
Reference:
[1] Chemistry - A European Journal, 2016, vol. 22, # 6, p. 2075 - 2084
39
[ 1717-59-5 ]
[ 135-19-3 ]
[ 75-46-7 ]
[ 712-79-8 ]
Reference:
[1] Journal of Fluorine Chemistry, 1989, vol. 44, p. 433 - 440
40
[ 135-19-3 ]
[ 118-03-6 ]
Reference:
[1] Patent: CN106866467, 2017, A,
41
[ 36592-58-2 ]
[ 135-19-3 ]
[ 2398-96-1 ]
Yield
Reaction Conditions
Operation in experiment
100 g
With tetrabutylammomium bromide; sodium carbonate In toluene for 5 h; Reflux
A solution of the compound N-methyl-N-(3-methylphenyl)thioformyl chloride represented by the formula D, dissolved in toluene 86.6ml, 56 g of 2-naphthol was added at room temperature, sodium carbonate 40 g, tetrabutylammonium bromide 0.8 g, toluene 200ml of toluene solution, after completion of the reaction, the reaction solution was heated to reflux for 5 h, cooled to room temperature after completion of the reaction, washed with water, dried, concentrated under reduced pressure and recrystallized from ethanol to give 100 g of the compound N-methyl-N-(3-methylphenyl) thiocarbamate as shown in formula E
Example 4 5 mol of beta-naphthol was charged into a tubular autoclave, along with 6 mol of dimethyl carbonate and 0.25 mol of <strong>[936-49-2]4,5-dihydro-2-phenylimidazole</strong>, and the mixture was heated to 140 C. After 2.5 hr, complete conversion of the betad-naphthol was determined by gas chromatography. After distillative refinement, 4.5 mol of beta-naphthyl methyl ether was obtained.
(i) Preparation of 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene 1,2-Dicyano-3,4,5,6-tetrachlorobenzene (30.5 parts), potassium carbonate (62.8 parts) and 2-naphthol (98.1 parts) were stirred in dimethylformamide (140 parts) at 70 C. for 3 hours. The mixture was poured into water (300 parts) and extracted with chloroform (3*300 parts). The combined chloroform extracts were washed with dilute aqueous sodium hydroxide solution (500 parts) and then with water (500 parts). The chloroform was dried over anhydrous magnesium sulphate before evaporating under reduced pressure to leave a brown liquid which crystallized on adding butan-1-ol, cooling and standing for 2 hours. The crystallized solid was filtered, washed with butan-1-ol until the filtrates were colourless. The solid was dried to give 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene (40.6 parts), m.p. 188-190 C.
With potassium carbonate; In N-methyl-acetamide;
(i) Preparation of 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene 1,2-Dicyano-3,4,5,6-tetrachlorobenzene (30.5 parts), potassium carbonate (62.8 parts) and 2-naphthol (98.1 parts) were stirred in dimethylformamide (140 parts) at 70C for 3 hours. The mixture was poured into water (300 parts) and extracted with chloroform (3 x 300 parts). The combined chloroform extracts were washed with dilute aqueous sodium hydroxide solution (500 parts) and then with water (500 parts). The chloroform was dried over anhydrous magnesium sulphate before evaporating under reduced pressure to leave a brown liquid which crystallized on adding butan-1-ol, cooling and standing for 2 hours. The crystallized solid was filtered, washed with butan-1-ol until the filtrates were colourless. The solid was dried to give 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene (40.6 parts) m.p. 188-190C.
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; NaH; In 1,4-dioxane;
EXAMPLE 3 Preparation of N-(2-naphthyl)-2-hydroxy-2-methylpropionamide. To a solution of 2-naphthol (533 mg, 3.70 mmol) in dioxane (20 mL) was added NaH (Aldrich, dry, 300 mg, 12.2 mmol) and Cs2 CO3 (4.00 g, 12.2 mmol). The resulting mixture was stirred at room temperature for about 30 minutes, then 2-bromo-2-methyl-propanamide (2.03 g, 12.2 mmol) was added and the resulting mixture was stirred at reflux for 16 h. After the reflux period, NMP (20 mL), DMPU (2 mL), and NaH (Aldrich, dry, 100 mg, 4.07 mmol) were added. The resulting mixture was stirred at 150 C. for 72 h. The reaction was cooled to room temp., and partitioned between water (50 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (100 mL) and the combined organics washed with water (2*50 mL), dried (Na2 SO4), and concentrated to about 3 g of material. The brown oil was chromatographed on silica (200 mL, 4 cm diam. column), eluding with 3:7 EtOAc/hexane to obtain N-(2-naphthyl)-2-hydroxy-2-methylpropionamide as a white solid (607 mg, 2.65 mmol, 71.6% yield).: mp 155-157 C. 1 H NMR (300 MHz, DMSO) delta 9.74 (br s, 1H, N--H), 8.41 (d, 1H, C1 --H, J =2.20 Hz), 7.86-7.76(om's, 4H), 7.49-7.37 (om's, 2H), 5.80 (br s, 1H, O--H), 1.40 (s, 6H, C(CH3)2); 13 C NMR (75 MHz, DMSO) delta 175.7, 136.2, 133.3, 129.8, 128.1, 127.4, 127.3, 126.3, 124.6, 120.6, 115.6, 72.5, 27.7; IR (KBr pellet) 1607, 1634, 1655 (amide C=O stretches), 3289 (NH/OH stretch); MS (CI/NH3) 247; Analysis: Calculated C 73.34 H 6.59 N 6.11 Found C 72.97 H 6.57 N 5.89.
EXAMPLE 2 At 150 C. and 100 mm Hg, 14 g of beta-naphthol and 9 g of dimethyl urethane were reacted in the presence of 0.7 g ZnCl2. A conversion of 2% of naphthol to methyl naphthyl urethane was obtained.
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; NaH; caesium carbonate; In 1,4-dioxane;
Example 3 Preparation of N-(2-naphthyl)-2-hydroxy-2-methylpropionamide. To a solution of 2-naphthol (533 mg, 3.70 mmol) in dioxane (20 mL) was added NaH (Aldrich, dry, 300 mg, 12.2 mmol) and Cs2CO3 (4.00 g, 12.2 mmol). The resulting mixture was stirred at room temperature for about 30 minutes, then <strong>[7462-74-0]2-bromo-2-methylpropanamide</strong> (2.03 g, 12.2 mmol) was added and the resulting mixture was stirred at reflux for 16 h. After the reflux period, NMP (20 mL), DMPU (2 mL), and NaH (Aldrich, dry, 100 mg, 4.07 mmol) were added. The resulting mixture was stirred at 150 C for 72 h. The reaction was cooled to room temp., and partitioned between water (50 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (100 mL) and the combined organics washed with water (2 x 50 mL), dried (Na2SO4), and concentrated to about 3 g of material. The brown oil was chromatographed on silica (200 mL, 4 cm diam. column), eluding with 3:7 EtOAc/hexane to obtain N-(2-naphthyl)-2-hydroxy-2-methylpropionamide as a white solid (607 mg, 2.65 mmol, 71.6% yield).: mp 155-157 C. 1H NMR (300 MHz, DMSO) delta 9.74 (br s, 1 H, N-H), 8.41 (d, 1 H, C1-H, J = 2.20 Hz), 7.86-7.76(om's, 4 H), 7.49-7.37 (om's, 2 H), 5.80 (br s, 1 H, O-H), 1.40 (s, 6 H, C(CH3)2); 13C NMR (75 MHz, DMSO) delta 175.7, 136.2, 133.3, 129.8, 128.1, 127.4, 127.3, 126.3, 124.6, 120.6, 115.6, 72.5, 27.7; IR (KBr pellet) 1607, 1634, 1655 (amide C=O stretches), 3289 (NH/OH stretch); MS (CI/NH3) 247; Analysis: Calculated C 73.34 H 6.59 N 6.11 Found C 72.97 H 6.57 N 5.89.
With aluminum (III) chloride; In 1,2-dichloro-ethane; at 80℃; for 1h;Inert atmosphere;
General procedure: A mixture of 2,3-dichloropyrazine or its derivatives (1, 1.0 equiv), substituted phenols (2a-p) (1.0 equiv) and anhydrous AlCl3 (1.0 equiv) in dichloroethane (5 mL) was stirred at 80 oC for 30 min. Then the mixture was cooled to room temperature and additional quantity of AlCl3 (1.0 equiv) was added. The mixture was stirred again at 80 oC for another 30 min. After completion of the reaction, the mixture was poured into ice-cold water (15 mL), stirred for 10 min and then extracted with ethyl acetate (3.x.5 mL). The organic layers were collected, combined, washed with water (3.x.10 mL), dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to afford the expected products.
With glucose sulfonic acid; In water; at 90℃; for 3h;
General procedure: A mixture of aromatic aldehydes (1, 2.0 mmol), dimedone (2, 2.0 mmol), 2-naphthol or beta-naphthylamine (3 or 4, 2.0 mmol) and 5 molpercent GSA was stirred in water (2 mL) at 90 °C until completely (monitored by TLC). After the completion, water (20?25 mL) was added to quench the reaction and then the reaction mixture was filtered, concentrated, the precipitate was collected, and purified by 95percent EtOH/DMF (8:1).
With potassium carbonate; In N,N-dimethyl acetamide; at 100℃; for 2h;
[0482] 2-Naphthol (20 g) was dissolved in N,N-dimethylacetamide (150 mL), potassium carbonate (28.7 g) and <strong>[138286-76-7]ethyl 2-bromooctanoate</strong> (52.2 g) were added thereto, and a reaction was carried out at 100 C. for 2 hours. Water (300 mL) and ethyl acetate (200 mL) were added to the reaction mixture, a separation was carried out, and the organic layer was concentrated; following this a 48 wt % sodium hydroxide aqueous solution (23 g), ethanol (50 mL), and water (50 mL) were added, and a reaction was carried out for 2 hours. The reaction mixture was poured into a 1N HCl aqueous solution (500 mL), and the crystals thus precipitated were filtered and washed with water, thus giving a crude carboxylic acid; following this, polyphosphoric acid (30 g) was added, and a reaction was carried out at 170 C. for 30 min. The reaction mixture was poured into water (300 mL), ethyl acetate (300 mL) was added, a separation was carried out, and the organic layer was concentrated and then purified by means of silica gel column chromatography, thus giving a ketone compound (10 g).
7-(2,3-dimethylphenyl)-6H,7H-naphtho[1,2:5,6]pyrano[3,2-c]chromen-6-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
With potassium 2-oxoimidazolidine-1,3-diide; In water; at 20℃; for 2h;Green chemistry;
General procedure: A mixture containing aldehyde (1 mmol), beta-naphthol (1 mmol; 1.44 g), 4-hydroxycoumarin (1 mmol; 1.62 g), 1mmol% of POImD and 10mL H2O were stirred at room temperature for the required reaction times. The progress of the reaction was monitored by TLC (EtOAc: petroleum ether 1:4). Having completed the reaction, we extracted the product with CHCl3/H2O. After separation of phases and evaporation of the organic phase and recrystallizationof the residue, the pure product was obtained. The aqueous phase was concentrated under reduced pressure to recover the catalyst for subsequent use.
With potassium fluoride; In acetonitrile; at 20 - 25℃; for 2h;
Thetetrafluoro Phthalo nitrile (compound (5)) 6.0 g (30mmol), and the potassiumfluoride 15 g (1.2eq.) and acetonitrile 20ml were put in the reactor in whichthe entrance of 100ml placing the thermometer was 4 and it was stirred and it cooledto 0. Here, beta - naphthol (compound(a-2)) 4.3 g (1.0eq.) was little by little injected. In 5 or less the mixture after theinput end, after it reacted at 1 hour the temperature was risen to 20 and it reacted 2 hours at 20 through 25. The solid emitting thereaction mixture to water and was segregated was filtered and it took out afterthe completion of reaction. The obtained preparation was well wiped off withthe methanol and the compound (4-2) 6.7g of the white solid was obtained(the yield 69percent).
69%
With potassium fluoride; In acetonitrile; at 5 - 20℃; for 3h;
A thermometer attached to a 100ml four-necked reactor, <strong>[1835-65-0]tetrafluorophthalonitrile</strong> (compound (5)) 6.0g (30mmol), potassium fluoride 21g (36mmol, 1.2 eq.) and acetonitrile into a 50ml, stirring under a 5 it cooled. Here, beta- naphthol (compound (a-1)) was added dropwise to 4.3g (30mmol, 1.0eq.). After the addition was completed, the mixture was reacted for 1 hour at less than 5, heated to room temperature and allowed to react for 2 hours. After the reaction, the reaction mixture was taken out by releasing the water, and filtering the precipitated solid. Resulting crude by well washing the product with isopropanol and dried to obtain the compound (4-1), 6.7g, as a white solid (yield 69percent).
7-(2,3-dimethylphenyl)-6H,7H-naphtho[1,2:5,6]pyrano[3,2-c]chromen-6-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With ammonium cerium (IV) nitrate; 1,2-dimethyl-3-[4-(1,2-dimethyl-1H-imidazol-3-ium-3-yl)butyl]-1H-imidazol-3-ium dibromide; In neat (no solvent); at 20℃; for 2.0h;
General procedure: A mixture containing benzyl alcohol(1 mmol), beta-naphthol (1 mmol), 4-hydroxycoumarin(1 mmol), 4 mmol % of [BDBDMIm]Br, and 0.05 g of CAN was stirred at room temperature for the requiredreaction times. Progress of the reaction was monitoredby TLC (EtOAc : petroleum ether, 1 : 3). Uponcompletion of the process the product was extractedwith CHCl3/H2O. The organic phases was separatedand the solvent evaporated. Crystallization of theresidue gave the pure product. The aqueous phase wasconcentrated under reduced pressure, washed withEt2O, and evaporated under reduced pressure torecover the ionic liquid for subsequent use.
N-(tert-butoxycarbonyl)-L-aspartic acid di-2-naphthyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
46%
With dmap; dicyclohexyl-carbodiimide; In hexane; ethyl acetate; at 5℃; for 5h;
General procedure: Dinaphthyl esters of N-Boc protected aminoacids were prepared by a general procedure starting from N-(tert-butoxycarbonyl)-L-amino acids. N,N'-Dicyclohexylcarbodiimide (0.42 g, 2 mmol) dissolved in dry hexane/EtOAc (1:1) mixture was added dropwise over 15 min to a stirred suspension of N-Boc-L-amino acid (1 mmol) in dry hexane/EtOAc (1:1) mixture at 5 C. To the reaction mixture 1- or 2-naphthol (0.29 g, 2 mmol) and a catalytic amount of 4-(dimethylamino)pyridine dissolved in dry hexane/EtOAc (1:1) mixture was added dropwise over 1 h. The mixture was stirred at 5 C over 4 h and then concentrated. The residue was stirred in Et2O (10 mL) and oxalic acid (0.3 g, 3.3 mmol) was introduced in portions to decompose excess DCC and precipitate DMAP. The mixture was filtered and evaporated under reduced pressure leaving oil, which was purified using radial chromatography on silica gel plates (2 mm thickness), using hexanes/EtOAc as moving phase.
N-[1-(4-methoxybenzyl)-2-oxo-1,2-dihydronaphtho[2,1-b]furan-1-yl]-4-chlorobenzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
General procedure: A mixture of aryl aldehyde (0.5 mmol), hippuric acid (0.5 mmol),acetic anhydride, (1.1 mmol) and Nafion-HSPIONs (80 mg,0.38 mol%) was subjected to MW irradiation for 15 min (800 W,90 C). Afterwards, beta-naphthol (0.5 mmol) was added and the resulting mixture was subjected to MW irradiation (800 W, 90 C)under solvent-free conditions for the appropriate time, according toTable 2. The reaction progress was monitored by TLC (hexane:ethylacetate, 2:1). After reaction completion, the mixture was cooled tor.t. and EtOH (20 mL) was added. The catalyst was removed using an external magnetic field. The solvent was evaporated and the crude products were purified by recrystallisation from hexane:ethyl acetate(4:1) to give the pure products in 65-96% yields.
N-[1-(4-methylbenzyl)-2-oxo-1,2-dihydronaphtho[2,1-b]furan-1-yl]-4-chlorobenzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73%
General procedure: A mixture of aryl aldehyde (0.5 mmol), hippuric acid (0.5 mmol),acetic anhydride, (1.1 mmol) and Nafion-HSPIONs (80 mg,0.38 mol%) was subjected to MW irradiation for 15 min (800 W,90 C). Afterwards, beta-naphthol (0.5 mmol) was added and the resulting mixture was subjected to MW irradiation (800 W, 90 C)under solvent-free conditions for the appropriate time, according toTable 2. The reaction progress was monitored by TLC (hexane:ethylacetate, 2:1). After reaction completion, the mixture was cooled tor.t. and EtOH (20 mL) was added. The catalyst was removed using an external magnetic field. The solvent was evaporated and the crude products were purified by recrystallisation from hexane:ethyl acetate(4:1) to give the pure products in 65-96% yields.
General procedure: To a mixture of compound 3(1.5 mmol) and 3M HCl (1.53 mL) at 0 °C, a solution of sodium nitrite (NaNO2, 1.58mmol) in water (3 mL) was added dropwise while maintaining the temperaturebelow 5 °C. After stirring for 30 min, asolution of diazonium chloride was prepared. Subsequently, a solution ofdiazonium chloride was added gradually to a mixture of phenols/anilines (4a,b; 6a?f;8a?k or 9a?e, 1.5 mmol), and ethanol (3 mL) at 0-5 °C. The reaction mixture was adjusted to pH 8-9 with 1 Maq. NaOH. After addition, the mixture was continued to stir for 3-6 h. Thesolid was collected, washed with water (3×15 mL), dried and purified by PTLC orsilica gel column chromatography to give the target products IIa?x.
(E)-1-[[4-(1H-imidazol-1-yl)phenyl]diazenyl]naphthalen-2-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
General procedure: A mixture of aniline derivative 1a-1e (1 mmol) and 1 cm3concentrated hydrochloric acid was thoroughly stirred atroom temperature for 15 min and then cooled to 0 C. Asolution containing 0.069 g sodium nitrite (1 mmol) in 10 cm3 water was added dropwise to the initial mixtureduring 40 min. An aqueous solution of aromatic nucleophile(1 mmol) in NaOH 10% (5 cm3) was then addedand the resulted mixture was stirred for 1 h at 0 C. Theprecipitated solid was filtered, washed with water and dried in air. The products 2a-2c, 2e, 2f, 2m, and 2o were purifiedby recrystallization in ethanol, but preparative TLC (nhexane-EtOAc, 4:1) was applied for purification of products2d, 2g-2l, 2n, and 2p.
(E)-1-[[4-(1H-pyrazol-1-yl)phenyl]diazenyl]naphthalen-2-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
71%
General procedure: A mixture of aniline derivative 1a?1e (1 mmol) and 1 cm3concentrated hydrochloric acid was thoroughly stirred atroom temperature for 15 min and then cooled to 0 C. Asolution containing 0.069 g sodium nitrite (1 mmol) in 10 cm3 water was added dropwise to the initial mixtureduring 40 min. An aqueous solution of aromatic nucleophile(1 mmol) in NaOH 10percent (5 cm3) was then addedand the resulted mixture was stirred for 1 h at 0 C. Theprecipitated solid was filtered, washed with water and dried in air. The products 2a?2c, 2e, 2f, 2m, and 2o were purifiedby recrystallization in ethanol, but preparative TLC (nhexane?EtOAc, 4:1) was applied for purification of products2d, 2g?2l, 2n, and 2p.