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Chemical Structure| 959-66-0
Chemical Structure| 959-66-0
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Product Details of [ 959-66-0 ]

CAS No. :959-66-0 MDL No. :MFCD00003084
Formula : C15H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XRZDIHADHZSFBB-UHFFFAOYSA-N
M.W : 239.27 Pubchem ID :70398
Synonyms :

Safety of [ 959-66-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 959-66-0 ]

* 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.

  • Downstream synthetic route of [ 959-66-0 ]

[ 959-66-0 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 94-02-0 ]
  • [ 62-53-3 ]
  • [ 959-66-0 ]
YieldReaction ConditionsOperation in experiment
91% With 1-butyl-3-methylimidazolium hydroxide; In toluene; at 120℃; for 2h; General procedure: A mixture of methyl/ethyl acetoacetate (0.58g, 5.0mmol), basic ionic liquid (0.78g, 5.0mmol), and an p-toluidine (0.64g, 6.0mmol) in toluene (1mL) was refluxed for 4h. The mixture was diluted with water (30mL) and extracted with ethylacetate or ether (3×10mL). The aqueous layer containing basic ionic liquid was recycled. The organic layer was stirred with 10% HCl (10mL) at room temperature for 2h. The organic layer was collected, washed with water (3×10mL), dried over anhydrous sodium sulphate, and concentrated under reduced pressure. The crude product was purified over silica-gel (60-120 mesh) using ethyl acetate-hexane (3:7) as eluent to afford 2a as colourless needles. Similar procedure was followed for other esters.
  • 2
  • [ 959-66-0 ]
  • [ 5855-57-2 ]
YieldReaction ConditionsOperation in experiment
100% With PPA; at 110℃; for 0.5h; Example 7; A/-(3-{1-[3-(4-Phenyl-quinolin-2-ylamino)-propyl]-piperidin-4-yl}-phenyl)-acetamide; Stepl; 4-Phenyl-quinolin-2-ol; 2- Benzoylacetanilide (200 mg, 0.80 mmol) were mixed with PPA (excess, solvent)and heated to 110 C and stirred for 30 minutes. The reaction mixture was cooledand then poured on ice. The title compound Example 7 Step 1 was collected as aprecipitate in quantitative yield.LCMS: Rt = 1.41min, m/z [MH+].
  • 4
  • [ 959-66-0 ]
  • [ 109-77-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
74% With ammonium acetate at 120℃; for 0.25h; General procedure for the synthesis of the 1,2-dihydropyridine derivatives 6a,b General procedure: Either of malononitrile (0.66 g, 0.01 mol) or ethyl cyanoacetate (1.13 g, 0.01 mol) together withammonium acetate (0.50 g) were added to a dry solid of compound 3 (2.16 g, 0.01 mol). Thereaction mixture, in each case, was heated in an oil bath at 120 oC for 15 min. The solid productformed after boiling with ethanol was collected by filtration.6-Hydroxy-2-imino-1,4-diphenyl-1,2-dihydropyridine-3-carbonitrile (6a). Yellow crystals(EtOH), yield 74% (2.12 g), mp 119-121 oC. IR max cm-1: 3544-3260, 3056, 2957, 2207, 1688,1662, 1604 (C=C). 1H NMR (DMSO-d6 400 MHz): = 4.15 (s, 2H, CH2), 7.30-7.99 (m, 10H,2C6H5), 10.21 (s, 1H, NH). 13C NMR (DMSO-d6 75 MHz): = 49.5 (pyridine C-3), 103.6,104.5 (C=C), 119.5 (CN), 120.19, 121.3, 123.9, 124.1, 124.8, 125.2, 125.5, 126.0, 134.5, 136.8(two benzene, pyridine C), 165.9 (C=O), 175.2 (C=N). EIMS m/z 287 [M]+ (20); anal. calcd. forC18H13N3O (287.11): C, 75.25; H, 4.56; N, 14.63. Found: C, 72.06; H, 4.72; N, 14.88.
30% With ammonium acetate; acetic acid In toluene for 20h; Heating;
  • 6
  • [ 7521-41-7 ]
  • [ 959-66-0 ]
  • 2-Phenyl-[1,8]naphthyridine-3-carboxylic acid phenylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With zirconyl chloride octahydrate; In neat (no solvent, solid phase); at 70 - 80℃; for 0.166667h; General procedure: A mixture of 2-aminonicotinaldehyde1 (0.01 mol) active methylene compound 2 (0.01 mol)and ZrOCl2.8H2O (0.01 mol) was ground by pestle andmortar at 70-80C for the period indicated in Table I. After completion of the reaction (monitored by TLC), the reaction mixture was treated with cold water. The solid separated was filtered, washed with water and purified by recrystallization from appropriate solvent to give 3 (Table I).
88% With indium(III) chloride; In neat (no solvent); at 20℃; for 0.125h; General procedure: A mixture of 2-aminonicotinaldehyde 1 (0.01 mol), active methylene compound 2 (0.01 mol) and InCl3 (0.01mol) was ground by pestle and mortar at RT for the period indicated in Table-1. On completion of the reaction as monitored by TLC, the reaction mixture was treated with cold water. The solid separated was filtered, washed with water and purified by recrystallization from appropriate solvent to afford 3 (Table-1).
88% With citric acid; In neat (no solvent); at 100℃; for 12h;Green chemistry; General procedure: A mixture of 2-aminonicotinaldehyde 1 (0.01 mol), active methylene compound 2 (0.01 mol) and citric acid (0.01 mol) was stirred at 100 under solvent-free conditions for appropriate time (Table-1). After completion of the reaction as indicated by TLC, the reaction mixture was diluted with cold water (5 ml). The solid that separated was filtered, washed with water and purified by recrystallization from appropriate solvent to afford 3 (Table-1).
  • 7
  • [ 959-66-0 ]
  • [ 5855-57-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; Example 42 4-Phenylcarbostyril To 20 ml of concentrated sulfuric acid, 16.4 g of 2-<strong>[959-66-0]benzoylacetanilide</strong> is added in portions at room temperature. The reaction is heated while maintaining the temperature at 105-120oC for 20 minutes. After cooling, the reaction is poured into ice, stirred for 1.5 hours and collected. The product is washed with water and dried to give 9.52 g of cream colored crystals, mp 258-261oC.
  • 8
  • [ 15424-14-3 ]
  • [ 959-66-0 ]
  • N,1,3,5-tetraphenyl-1H-pyrazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dmap; triethylamine; In dichloromethane; at 20℃; for 72h;Inert atmosphere; Green chemistry; A method for synthesizing a polysubstituted pyrazole compound, comprising the steps of:In a 25 mL tube reactor,The air was exchanged three times with nitrogen; (0.05 mmol, 12.0 mg), (0.10 mmol, 23.0 mg),Triethylamine (0.10 mmol, 10.1 mg) and DMAP (0.005 mmol, 1.2 mg) were weighed into the reaction tube in turn.Pumping in for nitrogen,And adding 0.3 mL of dichloromethane under a nitrogen atmosphere; reacting the reaction system at room temperature for 72 hours; after the TCL detection reaction is finished, directly adding silica gel, spin-drying column chromatography,A white solid was obtained (yield 90%).
  • 9
  • [ 959-66-0 ]
  • [ 5855-56-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: phosphoryl chloride
Multi-step reaction with 2 steps 1: phosphorus pentoxide; phosphoric acid / 6 h / 100 °C 2: trichlorophosphate; <i>N</i>,<i>N</i>-dimethyl-aniline / 4.5 h / 100 °C
Multi-step reaction with 2 steps 1: Polyphosphoric acid / 130 - 140 °C 2: trichlorophosphate; pyridine / 80 - 90 °C
Multi-step reaction with 2 steps 1: polyphosphoric acid / 6 h 2: trichlorophosphate / Alkaline conditions; Heating

  • 10
  • [ 4637-24-5 ]
  • [ 959-66-0 ]
  • [ 917837-67-3 ]
YieldReaction ConditionsOperation in experiment
61% In dichloromethane; at 20℃; A solution of 2-<strong>[959-66-0]benzoylacetanilide</strong> (Aldrich; 1.088 g, 4.55 mmol) in 15 mL of CH2Cl2 was treated with neat N,N-dimethylformamide dimethyl acetal (0.75 mL, 670 mg, 5.63 mmol). The reaction was allowed to stir at rt overnight. Concentration in vacuo gave a solid that was adsorbed onto 3.3 g of silica gel and added to 17 cm of flash silica gel in a 5 cm dia. column. Elution with 2 L of 4:1 EtOAc/hexanes afforded 797 mg (61%) of the desired compound as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 10.70 (br s, 1H), 7.64 (d, 2H, J=8.1 Hz), 7.59 (d, 2H, J=7.3 Hz), 7.48 (t, 1H, J=6.8 Hz), 7.44 (s, 1H), 7.42 (t, 1H, J=7.0 Hz), 7.30 (t, 2H, J=8.0 Hz), 7.04 (t, 1H, J=7.3 Hz), 3.01 (br s, 6H).
  • 11
  • [ 101-81-5 ]
  • [ 959-66-0 ]
  • [ 128316-23-4 ]
  • 13
  • [ 14871-92-2 ]
  • [ 959-66-0 ]
  • [Pd(PhNC(O)CH(COPh))(2,2'-bipyridine)] * 0.5 CH2Cl2 [ No CAS ]
  • 14
  • [ 121-69-7 ]
  • [ 959-66-0 ]
  • [ 51264-61-0 ]
YieldReaction ConditionsOperation in experiment
60% With rose bengal; In acetonitrile; for 24h;Irradiation; General procedure: A mixture of 1 (0.3 mmol), 2a (0.3 mmol) or 2b-d (1.5mmol) and Rose Bengal (1.0mol%) in MeCN (1.0mL) was stirred under irradiation of a 32W compact fluorescent light bulb (The parallel distance between the bulb and the reaction flask was about 2 cm) for the specified reaction time, and monitored by thin layer chromatography (TLC). The MeCN was removed under reduced pressure. The crude products were purified by column chromatography on silica gel (petroleum ether/EtOAc: 20/1-4/1) to give the desired products.
  • 15
  • [ 959-66-0 ]
  • (3S)-3-amino-N,3-diphenylpropanamide [ No CAS ]
  • 16
  • [ 201230-82-2 ]
  • [ 3282-32-4 ]
  • [ 62-53-3 ]
  • [ 959-66-0 ]
  • 17
  • [ 2314-97-8 ]
  • [ 959-66-0 ]
  • [ 1365265-15-1 ]
YieldReaction ConditionsOperation in experiment
45% With dihydrogen peroxide; iron(II) sulfate; In water; dimethyl sulfoxide; at 20℃; for 1h;Inert atmosphere; General procedure: A 30% H2O2 aqueous solution (2.0 mL) was added dropwise to the mixture of pentane-2,4-dione (10 mmol), DMSO (40 mL), 3.0 M DMSO solution of CF3I (10 mL), and 1.0 M aqueous solution of FeSO4 (3.0 mL) in an Ar atmosphere. The resulting mixture was stirred for 1 h at room temperature. After the reaction, an aliquot of the mixture was analyzed using 19F NMR, confirming the formation of 3-(trifluoromethyl)pentane-2,4-dione (1a) in 71% yield. The reaction mixture was poured into H2O and the product was extracted to diethyl ether. The diethyl ether layer was washed with a saturated aqueous solution of NaCl, dried with Na2SO4, and then concentrated by distillation. The product was isolated using silica gel chromatography.
  • 18
  • [ 2579-22-8 ]
  • [ 959-66-0 ]
  • [ 1416150-71-4 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; In tetrahydrofuran; at 65℃; for 10h;Green chemistry; General procedure: A mixture of beta-keto amide (0.2 mmol), ynal (0.2 mmol) and K2CO3 (30 mol%) in THF (1.0 mL) was placed in a test tube (10 mL) equipped with a magnetic stirring bar. The mixture was stirred at 65 C for 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.
  • 19
  • [ 1504-58-1 ]
  • [ 959-66-0 ]
  • [ 1416150-71-4 ]
  • 20
  • [ 764-01-2 ]
  • [ 959-66-0 ]
  • [ 1416150-80-5 ]
  • 21
  • [ 6261-22-9 ]
  • [ 959-66-0 ]
  • [ 1416150-82-7 ]
  • 22
  • [ 73922-81-3 ]
  • [ 959-66-0 ]
  • [ 1416150-83-8 ]
  • 23
  • [ 91-56-5 ]
  • [ 959-66-0 ]
  • [ 1448778-76-4 ]
YieldReaction ConditionsOperation in experiment
36% With ethylenediaminediacetic acid; In toluene; for 12h;Reflux; General procedure: Isatin having various substituents on the benzene ring reacting with beta-ketoamide to synthesis pyrrolo[3,4-c]quinoline-1,3-dione derivative by the method of sharing electrons to isatin. Derivative was synthesized by the method. isatin 1.1 mmol was dissolved in 8mL of toluene, beta- keto-amide 1.1 mmol, Ethylenediamine diacetate (EDDA) 8 mg, 0.1 mmol was added at room temperature. The reaction mixture was reflux for 4-12 hours and TLC (hexanes / EtOAc, 6: 1, v / v) and evaporation of the solvent when the desired reaction is complete, the remaining residue is hexane on silica gel / EtOAc (4: 1, v / v) of the flash column pyrrolo [3,4-c] quinoline-1,3-solid compound of the purified through chromatography using a variety of brown to give a derivative ions.
  • 27
  • [ 4648-54-8 ]
  • [ 959-66-0 ]
  • [ 940-38-5 ]
  • 28
  • 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
  • [ 959-66-0 ]
  • [ 112825-63-5 ]
  • 29
  • [ 83575-14-8 ]
  • [ 959-66-0 ]
  • methyl 5-hydroxy-2-phenyl-3-(phenylcarbamoyl)naphtho[1,2-b ]furan-4-carboxylate [ No CAS ]
  • 30
  • phenyl 1,4-dioxo-1,4-dihydronaphthalene-2-carboxylate [ No CAS ]
  • [ 959-66-0 ]
  • phenyl 5-hydroxy-2-phenyl-3-(phenylcarbamoyl)naphtho[1,2-b ]furan-4-carboxylate [ No CAS ]
  • 31
  • [ 69063-03-2 ]
  • [ 959-66-0 ]
  • 1-(7-chloroquinolin-4-yl)-N,5-diphenyl-1H-1,2,3-triazole-4-carboxamide [ No CAS ]
  • 32
  • [ 959-66-0 ]
  • [ 3800-65-5 ]
YieldReaction ConditionsOperation in experiment
With Selectfluor; In acetonitrile; at 100℃; for 2h; General procedure: The 1,3-dicarbonyl compounds (10 mmol) was added to a solution of Selectfluor (3.54 g, 10 mmol) in CH3CN (30 mL). After stirring at 100 C for 2h, the solvents were removed by rotary evaporation to provide raw products. The residue was then chromatographied on silica gel (eluent: hexane / ethyl acetate) to yield corresponding 2-fluoro-1,3-dicarbonyl compounds.
  • 33
  • [ 49619-82-1 ]
  • [ 959-66-0 ]
  • 2-[4-benzoyl-5-(phenylamino)furan-2-yl]carbonyl}phenol [ No CAS ]
  • 34
  • N-phenyl-N-(3-phenylprop-2-ynyl)hydroxylamine [ No CAS ]
  • [ 959-66-0 ]
  • 35
  • [ 622-37-7 ]
  • [ 959-66-0 ]
  • N,1,5-triphenyl-1H-1,2,3-triazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With diethylamine; In dimethyl sulfoxide; at 20℃; for 0.25h;Sonication; General procedure: beta-Oxo amides 1a-j (0.3mmol), aryl azides 2a-i (0.3mmol), Et2NH (5mol %) and DMSO (0.6mL) were added to a glass tube. The ultrasound probe was placed in a glass vial containing the reaction mixture. The amplitude of the ultrasound waves was fixed in 40%. Then, the homogeneous reaction mixture was sonicated for 15min. The crude product obtained was subsequently purified by column chromatography on silica gel using a mixture of hexane/ethyl acetate (5:1) as eluent to afford the desired products 3a-r.
62% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; at 20℃; for 24h;Inert atmosphere; In 25 ml in the test-tube reactor, purged with nitrogen 3 times, the substrate 1h (0.1mmol, 23.9 mg), phenyl nitrine (0.2mmol, 23.8 mg), DBU (0.01mmol, 1 . 52 mg) were added into reaction tube in sequence, and in the nitrogen atmosphere, added chlorofrom (0.3 ml), the reaction was stirred at room temperature for 24 hours. After the end of the detection reaction TCL, silica gel is directly added, turns on lathe the main column chromatography, to obtain white solid 3ia (62%).
  • 36
  • [ 536-74-3 ]
  • [ 959-66-0 ]
  • 1-hydroxy-N,4-diphenyl-2-naphthamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tert.-butylhydroperoxide; N-bromophthalimide; 2-bromoethylamine hydrobromide; In 1,4-dioxane; ethanol; at 90℃; for 20h;Sealed tube; Add phenylacetylene (1mmol, 102.1mg) in a reaction vessel, 2-benzoyl-acetanilide (0.5 mmol, 119.6mg), N- bromo phthalimide (0.1mmol, 22.6mg), bromo ethylamine hydrobromide (0.2mmol, 41.0mg), t-butyl hydroperoxide (1.75mmol, 157.7mg), a mixed solution of ethanol and 4mL 1,4- dioxane (v: v = 1: 1), sealing, 90 degree with stirring for 20 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and purified by column chromatography (eluent petroleum ether) to give 1-hydroxy-N, 4-diphenyl-2-naphthamide (11a) 141.5mg, 83% yield.
  • 37
  • 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
  • [ 959-66-0 ]
  • [ 112825-63-5 ]
  • α-(trifluoromethylthio)benzoylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Sodium hydride (7.9 mg, 0.33 mmol) was suspended in 1.0 ml of tetrahydrofuran under nitrogen,Then, 1.0 ml of a tetrahydrofuran solution of 2-<strong>[959-66-0]benzoylacetanilide</strong> (72 mg, 0.3 mmol) was added rapidly, and the reaction was carried out at room temperature for 0.5 hour.The reaction solution was then placed in an ice-water bath,A 1.0 ml portion of a tetrahydrofuran solution of the trifluoromethyl sulfide reagent (110 mg, 0.39 mmol) was rapidly added to the reaction system, and the reaction was continued at that temperature for 0.5 hour.After completion of the reaction, the temperature was raised to room temperature and the solvent was removed by rotary evaporation under reduced pressure. The residue was purified by flash silica gel column to obtain the corresponding products c9 and c9 '(85 mg, 83%). The purity was more than 95% by 1H-NMR.
  • 38
  • [ 95-54-5 ]
  • [ 959-66-0 ]
  • N,3-diphenylquinoxaline-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% General procedure: 10 mL Pyrex tube equipped with a magnetic stir bar was charged with 1a (0.1 mmol), 10 mol % Cu(NO3)2·2.5H2O, CH3CN (2 mL) in air at 50 oC for 1 hour then the mixture followed by the addition of 2a (0.2 mmol) at room temperature for 2 h. Then mixture was evaporated under reduced pressure to remove the solvent and the residue was purified by flash chromatography on silica gel (Petroleum ether/ EtOAc) to afford the desired product.
  • 39
  • 2,6-di-tert-butyl-4-(2-hydroxybenzylidene)cyclohex-2,5-diene-1-one [ No CAS ]
  • [ 959-66-0 ]
  • C36H41NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃; for 24h;Inert atmosphere; In 25 ml test tube in the reactor, nitrogen gas is used to exchange air 3 times. The substrate 1a (0.05 mmol, 15.5 mg), substrate 2i (0.06 mmol, 14 . 34 mg), DBU (0.0025 mmol, 0 . 38 mg) sequentially calls into reaction tube, evacuating nitrogen exchange, and in under the nitrogen atmosphere by adding dichloromethane (1.0 ml), the reaction at room temperature 24 hours. TCL detection after the reaction, direct and silica gel, turns on lathe the main column chromatography, to obtain white solid 3ai (97%).
  • 40
  • [ 99685-96-8 ]
  • [ 959-66-0 ]
  • C75H11NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) chloride; In 1,2-dichloro-benzene; acetonitrile; trifluoroacetic acid; at 120℃; for 12h;Sonication; Fullerene C60 (54.0 mg, 0.075 mmol) was first added to the dried reaction tube, CuCl (3.7 mg, 0.0375 mmol) and (0.15 mmol) were added to the reaction tube, and trifluoroacetic acid was added. The mixed solvent of acetonitrile and anhydrous dichlorobenzene was solubilized by ultrasonication, and then the plug was placed in a 120 C oil bath to stir the reaction for 12 hours (complete reaction was detected by TLC). The reaction mixture was filtered through a short silica gel column. In order to remove any insoluble material, the solvent was evaporated in vacuo and the remaining solid was dissolved with CS2. The sample was loaded and passed through the column. Unreacted fullerene C60 was first collected with CS2 as eluent, and the mixed solution of CS2 and DCM was used as washing. The stripping agent was eluted to give the target product 2d.
  • 41
  • [ 13781-33-4 ]
  • [ 959-66-0 ]
  • 3-benzoyl-1-phenyl-4-(thiophen-2-yl)pyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate; In tetrahydrofuran; at 65℃; for 10h;Green chemistry; General procedure: A mixture of beta-keto amide (0.2 mmol), ynal (0.2 mmol) and K2CO3 (30 mol%) in THF (1.0 mL) was placed in a test tube (10 mL) equipped with a magnetic stirring bar. The mixture was stirred at 65 C for 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.
  • 42
  • [ 1846-68-0 ]
  • [ 959-66-0 ]
  • 3-benzoyl-4-pentyl-1-phenylpyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In tetrahydrofuran; at 65℃; for 10h;Green chemistry; General procedure: A mixture of beta-keto amide (0.2 mmol), ynal (0.2 mmol) and K2CO3 (30 mol%) in THF (1.0 mL) was placed in a test tube (10 mL) equipped with a magnetic stirring bar. The mixture was stirred at 65 C for 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.
  • 43
  • [ 119-65-3 ]
  • [ 109-92-2 ]
  • [ 959-66-0 ]
  • 2-benzoyl-4-ethoxy-4-(isoquinolin-1-yl)-N-phenylbutanamide [ No CAS ]
  • 44
  • [ 959-66-0 ]
  • [ 109-77-3 ]
  • [ 2304985-89-3 ]
YieldReaction ConditionsOperation in experiment
90% With sulfur; triethylamine In 1,4-dioxane for 3h; Reflux; General procedure for the synthesis of the thiophene derivatives 13a,b General procedure: Each of elemental sulfur (0.32 g, 0.01 mol) and either malononitrile (0.66 g, 0.01 mol) or ethylcyanoacetate (1.13 g, 0.01 mol) was added to a solution of compound 3 (2.16 g, 0.01 mol) in1,4-dioxane (40 mL) containing triethylamine (0.50 mL). The reaction mixture, in each case,was heated under reflux for 3 h then poured onto ice/water containing few drops of hydrochloricacid and the formed solid product was collected by filtration. 5-Amino-4-cyano-N,3-diphenylthiophene-2-carboxamide (13a). Orange crystals (1,4-dioxane),yield 90% (2.87 g), mp 120-122 oC. IR max cm-1:3439-33259, 3056, 2923, 2211, 1687. 1HNMR (DMSO-d6 400 MHz): = 4.15 (s, 2H, D2O exchangeable, NH2), 7.31-7.58 (m, 10H,2C6H5), 10.21 (s, 1H, D2O exchangeable, NH), .13C NMR (DMSO-d6 75 MHz): = 117.5 (CN),120.3, 121.6, 122.8, 123.6, 124.4, 124.8, 125.1, 125.8, 136.7, 139.5. 140.4, 142.2 (two benzeneC, thiophene C), 165.8 (C=O). EIMS m/z 319 [M]+ (26). Anal. calcd. for C18H13N3OS (319.38):C, 67.69; H, 4.10; N, 13.16; S, 10.04. Found: C, 67.56; H, 3.89; N, 12.88; S, 10.38.
65.8% With sulfur; triethylamine In ethanol for 3h; Reflux;
  • 45
  • [ 105-56-6 ]
  • [ 959-66-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
73% With sulfur; triethylamine In 1,4-dioxane for 3h; Reflux; General procedure for the synthesis of the thiophene derivatives 13a,b General procedure: Each of elemental sulfur (0.32 g, 0.01 mol) and either malononitrile (0.66 g, 0.01 mol) or ethylcyanoacetate (1.13 g, 0.01 mol) was added to a solution of compound 3 (2.16 g, 0.01 mol) in1,4-dioxane (40 mL) containing triethylamine (0.50 mL). The reaction mixture, in each case,was heated under reflux for 3 h then poured onto ice/water containing few drops of hydrochloricacid and the formed solid product was collected by filtration. 5-Amino-4-cyano-N,3-diphenylthiophene-2-carboxamide (13a). Orange crystals (1,4-dioxane),yield 90% (2.87 g), mp 120-122 oC. IR max cm-1:3439-33259, 3056, 2923, 2211, 1687. 1HNMR (DMSO-d6 400 MHz): = 4.15 (s, 2H, D2O exchangeable, NH2), 7.31-7.58 (m, 10H,2C6H5), 10.21 (s, 1H, D2O exchangeable, NH), .13C NMR (DMSO-d6 75 MHz): = 117.5 (CN),120.3, 121.6, 122.8, 123.6, 124.4, 124.8, 125.1, 125.8, 136.7, 139.5. 140.4, 142.2 (two benzeneC, thiophene C), 165.8 (C=O). EIMS m/z 319 [M]+ (26). Anal. calcd. for C18H13N3OS (319.38):C, 67.69; H, 4.10; N, 13.16; S, 10.04. Found: C, 67.56; H, 3.89; N, 12.88; S, 10.38.
62.75% With sulfur; triethylamine In ethanol for 3h; Reflux;
  • 46
  • [ 868-54-2 ]
  • [ 959-66-0 ]
  • [ 2582030-75-7 ]
YieldReaction ConditionsOperation in experiment
86% In 1,4-dioxane at 120℃; for 6h; Alkaline conditions; 2,4-Diamino-7-oxo-5,8-diphenyl-7,8-dihydro-1,8-naphthyridine-3-carbonitrile (9) 2-Aminoprop-1-ene-1,1,3-tricarbonitrile (8) (1.32 g, 0.01 mol) was added to a solution ofcompound 3 (2.16 g, 0.01 mol) in 1,4-dioxane (40 mL) containing triethylamine (0.50 mL). Thereaction mixture was heated under reflux for 6 h then evaporated under vacuum. The solidproduct produced after triturating the remaining product with diethyl ether was collected byfiltration. Pale yellow crystals (1,4-dioxane), yield 86% (3.03 g), mp 260-263 oC. IR max cm-1:3473, 3327, 3056, 2220, 1688, 1623. 1H NMR (DMSO-d6, 400 MHz) = 4.92, 5.68 (2s, 4H,D2O exchangeable, 2NH2), 6.80 (s, 1H pyridine H-6), 7.31-7.58 (m, 10H, 2C6H5). 13C NMR(DMSO-d6, 75 MHz): = 116.8 (CN), 120.1, 121.3, 122.3, 123.5, 124.0, 124.8, 125.1, 126.4,128.1, 130.2, 131.2, 131.8, 133.2, 134.2 (two C6H5, two pyridine C), 162.4 (C=O), 169.5 (C=N).EIMS m/z 353 [M]+ (22). Anal. calcd. for C21H15N3O (353.39): C, 71.38; H, 4.28; N, 19.82.Found: C, 71.42; H, 4.31; N, 19.72.
  • 47
  • [ 959-66-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
68.2% With Ru(OCOCH3)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; hydrogen; 2,2,2-trifluoroacetic acid ammonia In tetrahydrofuran at 90℃; Autoclave;
  • 48
  • [ 62-53-3 ]
  • [ 196930-90-2 ]
  • [ 959-66-0 ]
YieldReaction ConditionsOperation in experiment
65% With tert.-butylhydroperoxide; iron(III) chloride In water; acetonitrile at 80℃; for 2h; Inert atmosphere; General procedure for preparation of compounds 3 or 4 General procedure: To a Schlenk tube equipped with a rubber septum was successively added acylhydrazine 1 (1 mmol), amine 2 (1 mmol), FeCl3 (16.2 mg, 10 mol %) and acetonitrile (10 mL). The tube was evacuated and purged with argon three times. Then TBHP (70% in H2O (6 mmol), was slowly added and the mixture allowed to stir for 2 hours at 80 oC. After the completion of reaction (indicated by TLC), the reaction mixture was concentrated under reduced pressure and the crude mixture was purified by column chromatography using acetone/petroleum ether (v/v 1:10) as eluent to obtain the pure products 3 or 4.
  • 49
  • [ 621-03-4 ]
  • [ 98-80-6 ]
  • [ 959-66-0 ]
YieldReaction ConditionsOperation in experiment
80% With [2,2]bipyridinyl; palladium diacetate; trifluoroacetic acid In tetrahydrofuran at 80℃; General procedure for synthesis of β-ketoamides (4a-4d): General procedure: In oven dried 5 mL vial contains the mixture of 2-cyano-(N-tolyl)-acetamide (30 mg, 0.17 mmol, 1.0 equiv.) arylboronic acid (2 equiv.), bipyridine (3 mg, 10 mol%), Pd(OAc)2 (5 mg. 10 mol%) were dissolved in THF solvent (2 mL). To this stirred solution, TFA (61 μl, 4 equiv.) was added and the reaction mixture was stirred vigorously at 80 oC for 22-30 hours. After complete consumption of the starting material (monitored by TLC), the reaction mixture was cooled to room temperature. Then the contents were poured into a separating funnel (25 mL) containing 5 mL of water. The work-up procedure was followed similar to the synthesis of 3a-3c. The crude compound was purified by flash column chromatography (100-200 Mesh size silica gel). Compound will elute in 20% EtOAc/Hexane (Rf = 0.6).
  • 50
  • [ 98-86-2 ]
  • [ CAS Unavailable ]
  • [ 959-66-0 ]
YieldReaction ConditionsOperation in experiment
71.28% With potassium <i>tert</i>-butylate In toluene at 110℃; Inert atmosphere; 7. 3-oxo-N,3-diphenylpropanamide (959-66-0) (3ag) General procedure: To a stirred solution of a acetophenone (1 mmol), and 1,4,2-Dioxazol-5-ones (1.2 mmol) intoluene (2 ml) was added potassium tert-butoxide (2.0 mmol) in one portion at room temperature.The mixture was stirred at 110 °C for 1 to 2 hr. After completion of the reaction, themixture was cooled to room temperature and water (5 ml) was added. The reaction mixturewas extracted with ethyl acetate (10ml x 3) and the combined organic layers was dried oversodium sulfate. The solvent was removed under reduced pressure and the residue was purifiedby silica gel chromatography using hexane/ethyl acetate as eluent to afford the correspondingβ-ketoamides.
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