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CAS No. : | 4424-17-3 | MDL No. : | MFCD00017096 |
Formula : | C13H12N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FDPVTENMNDHFNK-UHFFFAOYSA-N |
M.W : | 212.25 | Pubchem ID : | 78142 |
Synonyms : |
2-Amino-N-phenylbenzamide
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
95% | With iodine at 80℃; for 0.75h; Ionic liquid; | |
86% | With (2,3,4,5,6-pentafluorophenyl)ammonium triflate for 0.1h; Microwave irradiation; neat (no solvent); | |
84% | With sulfuric acid; silica gel for 0.0833333h; Heating; microwave irradiation; |
83% | With HY-zeolite for 0.116667h; Neat (no solvent); Microwave irradiation; | |
72% | With aluminium trichloride; silica gel; zinc(II) chloride for 0.1h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With acetic acid In ethanol at 110℃; for 24h; Inert atmosphere; Sealed tube; | 3.2.2. Method 2 General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2-3 equiv) and absolute ethanol (2-3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12-72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5%ether in pentane. The following compounds were prepared: |
87% | With Montmorillonite K-10 clay for 0.1h; microwave irradiation; | |
85% | With sulfuric acid; silica gel for 0.0833333h; Heating; microwave irradiation; |
84% | With (2,3,4,5,6-pentafluorophenyl)ammonium triflate Microwave irradiation; neat (no solvent); | |
82% | for 5h; Heating / reflux; | 4.B A mixture of 2-amino-N-phenyl-benzamide 26 (2 g, 0.009 mol) and 1,1,1-triethoxy-ethane (5.2 mL, 0.028 mol) were heated for 5 hours. The reaction mixture was poured into water, filtered off, washed with water yielding 2-methyl-3-phenyl-3H-quinazolin-4-one 27 (1.6 g, 82%). After recrystallization it was used in next step without further purification. |
79% | With HY-zeolite for 0.116667h; Neat (no solvent); Microwave irradiation; | |
for 5h; Heating; | 4 2-Methyl-3-phenyl-3H-quinazolin-4-one (27) 2-Methyl-3-phenyl-3H-quinazolin-4-one (27). A mixture of 2-amino-N-phenyl-benzamide 26 (2 g, 0.009 mol) and 1,1,1-triethoxy-ethane (5.2 mL, 0.028 mol) were heated for 5 hours. The reaction mixture was poured into water, filtered off, washed with water yielding 2-methyl-3-phenyl-3H-quinazolin-4-one 27 (1.6 g, 82%). After recrystallization it was used in next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With potassium carbonate;tris-(dibenzylideneacetone)dipalladium(0); | Example 72 2-Phenylaminobenzamide and 2-amino-N-phenylbenzamide Using t-amyl Alcohol as Solvent An oven-dried resealable schlenk tube containing a stir bar was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl (19.0 mg, 0.04 mmol), 2-aminobenzamide (102 mg, 0.75 mmol) and K2CO3 (173 mg, 1.25 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon. Bromobenzene (55 muL, 0.5 mmol) and tamyl alcohol (1 mL) were added through the septum via syringe. The septum was replaced with a Teflon screw cap. The schlenk tube was sealed and put into a pre-heated oil bath at 110 C. The reaction mixture was stirred for 15 h, allowed to cool down to room temperature. GC analysis showed full conversion of bromobenzene. 2-Phenylaminobenzamide was obtained in 65% GC yield and 2-amino-N-phenylbenzamide in 10% GC yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With toluene-4-sulfonic acid In dichloromethane Darkness; Reflux; | General procedure for the synthesis of2,3-dihydro-4(1H)-quinazolinones (GP-2) General procedure: 1.2 equiv of appropriate aldehyde was added to a solution of aminobenzamide in CH2Cl2. To this, 2-5% by weight of p-TsOH was added and refluxed. The reactions were carried out in the absence of light due to possible degradation reactions[3]; the reaction was monitored by TLC (hexane:EtOAc 6:4). A final straw yellow solution was obtained and the crude reaction mixture was purified by flash chromatography eluting with hexane:EtOAc, 9:1-6:4.2.3 |
97% | With toluene-4-sulfonic acid In dichloromethane Reflux; Darkness; | 2.2. General procedure for the synthesis of2,3-dihydro-4(1H)-quinazolinones (GP-2) General procedure: 1.2 equiv of appropriate aldehyde was added to a solution ofaminobenzamide in CH2Cl2. To this, 2-5% by weight of p-TsOH wasadded and refluxed. The reactions were carried out in the absenceof light due to possible degradation reactions[3]; the reaction wasmonitored by TLC (hexane:EtOAc 6:4). A final straw yellow solutionwas obtained and the crude reaction mixture was purified by flashchromatography eluting with hexane:EtOAc, 9:1-6:4 |
97% | With toluene-4-sulfonic acid In dichloromethane for 6h; Reflux; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene at 70℃; for 24h; | |
With N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Inert atmosphere; Glovebox; | 1.B B-Synthesis of 4-Quinazolinone Derivatives from Functionalized Aromatic Amines B-Synthesis of 4-Quinazolinone Derivatives from Functionalized Aromatic AminesThe following results describe the synthesis of 4-quinazolinone derivatives from aromatic amines functionalized in ortho position by amides (anthranilamides). In this case, the amine R1NH2 and the nitrogenous nucleophile R5R6NH (in this case an amide) are two reactive functional groups of one and the same molecule (diamine) and are thus connected via a covalent bond. This bond is preferably an aromatic ring of benzene, pyridine or pyrimidine type and the ring formed during the reaction is a nitrogenous heterocycle comprising 6 atoms. The results presented in table 2 were obtained by preferably using polymethylhydrosiloxane (PMHS) as reducing agent, the latter proving to be more effective with regard to these reactants than phenylsilane (PhSiH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
145 mg | With scandium tris(trifluoromethanesulfonate); In methanol; at 100℃; for 1h;Microwave irradiation; | General procedure: The nitrobenzamide intermediate (0.5mmol) was dissolved in methanol (2.5mL). To the solution was added 10% Pd/C (75mg) and ammonium formate (32mg, 0.5mmol). After 1h the reaction was filtered, rinsing with methanol. The filtrate was adjusted to a volume 1mL in methanol and then treated with an aldehyde (0.55mmol) and scandium(III) triflate (0.05) mmol. The reaction was microwave irradiated at 100C for 1h, after which the solvent was removed in vacuo. The product dihydroquinazolinones were isolated by silica gel flash chromatography with a hexanes/ethyl acetate solvent gradient. The chromatographed products were subsequently purified by recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36%; 59.4% | for 24h; | Synthesis of Retro-2 and Retro-2cycl [00281] To a stirring solution of 2-aminobenzanilide was added 5-methyl-2- thiophenecarboxaldehyde (86.3 mu, .80 mmol). After 24 hours, the reaction was concentrated and then chromatographed on silica gel with 20-40% ethyl acetate in hexanes. Retro-2 and Retro-2cycl were cleanly separated and then further purified by recrystalization from ethanol and ethyl acetate respectively. Yields: Retro-2 47.2 mg (36%), Retro-2cycl 78.0 mg (59.4%). Characterization: Retro-2 FAB HRMS: Ci9Hi6N2OSNa+ Predicted: 343.0881 Found: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With oxygen In dimethyl sulfoxide at 120℃; for 48h; | 3. Substrate Scope for 2,3-Disubstituted-4(3H)-quinazolinones 8 General procedure: An N-substituted anthranilamide 7 (1.0 mmol; 1.0 equiv.) and an aldehyde 2 (1.2 mmol; 1.2 equiv.) were dissolved in DMSO (5 mL). Then, the reaction mixture was stirred at 120 oC in an open flask and monitored by TLC. After complete consumption of the starting materials, the reaction mixture was poured onto water and extracted with methylene chloride. The organic layer was combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude mixture was purified by column chromatography on silica using hexanes / ethyl acetate (5:1) as an eluent to afford 2,3-disubstituted-4(3H)-quinazolinone 8. |
30% | With oxygen; toluene-4-sulfonic acid In water; chlorobenzene at 110℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃; | Synthesis of 4(3H)-Quinazolinone Derivatives 5: General Procedure General procedure: A mixture of dimethyl formamide DMF 1 (60 mmol, 4.6 mL) and phosphorusoxychloride POCl3 2 (60 mmol, 5.6 mL) was stirred at room temperature for 35 min.Then, 2-aminobenzamide derivatives 4 (2 mmol) were added to the reaction mixture and the stirring was continued for 8-12 h. Upon completion of reaction (checked byTLC), the solution was added to water and extracted with ethyl acetate (350 mL).The organic layer was separated, dried (Na2SO4), and concentrated in vacuo to yield the crude product, which was purified by recrystallization from ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With di-tert-butyl peroxide; toluene-4-sulfonic acid at 110℃; for 20h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
125 mg | With scandium tris(trifluoromethanesulfonate) In methanol at 100℃; for 1h; Microwave irradiation; | 4.7. Dihydroquinazolinone synthesis 4.7.1. General procedure A. General procedure: The nitrobenzamide intermediate (0.5mmol) was dissolved in methanol (2.5mL). To the solution was added 10% Pd/C (75mg) and ammonium formate (32mg, 0.5mmol). After 1h the reaction was filtered, rinsing with methanol. The filtrate was adjusted to a volume 1mL in methanol and then treated with an aldehyde (0.55mmol) and scandium(III) triflate (0.05) mmol. The reaction was microwave irradiated at 100°C for 1h, after which the solvent was removed in vacuo. The product dihydroquinazolinones were isolated by silica gel flash chromatography with a hexanes/ethyl acetate solvent gradient. The chromatographed products were subsequently purified by recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With 1H-imidazole; copper(II) acetate monohydrate In chlorobenzene at 120℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With iodine; oxygen; ammonium chloride In dimethyl sulfoxide at 120℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With tert.-butylhydroperoxide; caesium carbonate; acetic acid; potassium iodide In water at 120℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube | ||
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube | ||
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube |
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube | ||
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube | ||
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube | ||
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube | ||
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube | ||
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 60 °C 2: tert.-butylhydroperoxide; caesium carbonate / acetonitrile; water / 10 h / 80 °C | ||
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / ethanol / 20 °C / Reflux 2: cesium acetate; copper dichloride / ethanol / 5 h / 25 °C / Irradiation | ||
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; tetrabutylammonium perchlorate / acetonitrile / 3 h / 20 °C 2: toluene-4-sulfonic acid; tetrabutylammonium perchlorate / acetonitrile / 1.5 h / 20 °C / Electrolysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(I) oxide; tricyclohexylphosphine In chloroform at 100℃; for 24h; Schlenk technique; Sealed tube; | General procedure: A reaction tube was charged under air with 2-aminobenzanilide(1a, 0.2 mmol), Et3N (2a, 0.6 mmol), Cu2O (10 mol%), PCy3(10 mol%), and CHCl3 (2 mL). The vessel was sealed, heated at100 °C (oil-bath temperature) for 24 h, and then cooled to r.t.DDQ (1 equiv) was added, and the mixture was kept at r.t. for 1h. After filtration of the mixture and evaporation of the solventunder reduced pressure, the crude product was purified by column chromatography [silica gel, hexane-EtOAc (3:1)] to givea light-yellow solid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(I) oxide; tricyclohexylphosphine In chloroform at 100℃; for 24h; Schlenk technique; Sealed tube; | General procedure: A reaction tube was charged under air with 2-aminobenzanilide(1a, 0.2 mmol), Et3N (2a, 0.6 mmol), Cu2O (10 mol%), PCy3(10 mol%), and CHCl3 (2 mL). The vessel was sealed, heated at100 °C (oil-bath temperature) for 24 h, and then cooled to r.t.DDQ (1 equiv) was added, and the mixture was kept at r.t. for 1h. After filtration of the mixture and evaporation of the solventunder reduced pressure, the crude product was purified by column chromatography [silica gel, hexane-EtOAc (3:1)] to givea light-yellow solid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(I) oxide; tricyclohexylphosphine; In chloroform; at 100℃; for 24h;Schlenk technique; Sealed tube; | General procedure: A reaction tube was charged under air with 2-aminobenzanilide(1a, 0.2 mmol), Et3N (2a, 0.6 mmol), Cu2O (10 mol%), PCy3(10 mol%), and CHCl3 (2 mL). The vessel was sealed, heated at100 C (oil-bath temperature) for 24 h, and then cooled to r.t.DDQ (1 equiv) was added, and the mixture was kept at r.t. for 1h. After filtration of the mixture and evaporation of the solventunder reduced pressure, the crude product was purified by column chromatography [silica gel, hexane-EtOAc (3:1)] to givea light-yellow solid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(I) oxide; tricyclohexylphosphine; In chloroform; at 100℃; for 24h;Schlenk technique; Sealed tube; | General procedure: A reaction tube was charged under air with 2-aminobenzanilide(1a, 0.2 mmol), Et3N (2a, 0.6 mmol), Cu2O (10 mol%), PCy3(10 mol%), and CHCl3 (2 mL). The vessel was sealed, heated at100 C (oil-bath temperature) for 24 h, and then cooled to r.t.DDQ (1 equiv) was added, and the mixture was kept at r.t. for 1h. After filtration of the mixture and evaporation of the solventunder reduced pressure, the crude product was purified by column chromatography [silica gel, hexane-EtOAc (3:1)] to givea light-yellow solid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With iodine at 50℃; for 7h; Ionic liquid; Inert atmosphere; Green chemistry; chemoselective reaction; | General procedure for the syntheses of 3 General procedure: A dry 50-mL flask was charged with 2-aminobenzamide 1 (1.0 mmol) and 1,2-dicarbonyl compound 2 (1.0 mmol), iodine (13 mg, 0.05 mmol), and [BMIm]Br (2.0 mL). The reaction mixture was stirred at 50 °C under anhydrous atmosphere for 6-10 h. After the completion of the reaction as indicated by TLC [a small amount of reaction mixture was dissolved in EtOH, and the developing solvent is a mixture of ethyl acetate and petroleum ether (volume ratio 3:1)], 5 mL water was added to the mixture. The yellow precipitate was filtered off and purified by recrystallization from 95% EtOH to give final product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 2,2,2-trifluoroethanol at 20℃; for 0.116667h; Green chemistry; | General procedure for the synthesis of isoindolo[2,1-a]quinazolines (4a-4l) General procedure: A mixture of an equimolar quantities of 2-aminobenzamides (1 mmol), 2-carboxybenzaldehyde (1 mmol) and TFE (0.5 mL) was ground together for 9-11 min using a mortar and pestle at room temperature. The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was washed with petroleum ether followed by CHCl3, and then filtered to obtain the pure products. |
87% | With choline chloride; toluene-4-sulfonic acid at 20℃; for 1h; Green chemistry; | 6,6a-Dihydroisoindolo[2,1-a]quinazoline-5,11-diones 3a-g, Isoindolo[2,1-a]pyrrolo[2,1-c]quinoxalin-10(14bH)-ones 5a-f, and Indolo[1,2-a]isoindolo[1,2-c]quinoxalin-11(15bH)-ones 7a,b; General Procedure General procedure: To a mixture of 2-formylbenzoic acid (1; 1 mmol) and the appropriate amine 2, 4, or 6 (1 mmol) was added the DES (1.5 g), prepared from ChCl and TsOH.31 The resulting mixture was stirred at r.t. until the starting materials were completely consumed (TLC). The reaction mass was then diluted with H2O (5mL), and the desired product, obtained as a precipitate, was isolated by filtration and crystallized from the appropriate solvent.The filtrate was evaporated under vacuum at 70 °C for 2 h, and the residual DES was reused in further reaction cycles. |
83% | With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene Reflux; | Synthesis of quinazolinones (general procedure). General procedure: To a solution of amino amide (0.005 mol) in a xylene-acetic acid (1 : 1) mix-ture (10 mL), 0.005 mol of the corresponding aldehyde (0.01 mol for the synthesis of compound 22) was added and the mixture was re uxed for 3-5 h (TLC control by aldehyde). After keeping under these conditions, the solvent was removed in vacuo, 2% hydrochloric acid was added to the residue, and the precipitate that formed was ltered off . The lter precipitate was washed with 5% soda solution and water and, if necessary, recrystallized from aqueous ethanol. The yields and physicochemical characteristics of 2-aryl quinazolinones 11a-y, 12a-l, 13a,b, 16, 18a,b, and 22a-f are given in Tables 2 and 3. |
80% | With sulfonic acid functionalized SBA-15 mesoporous silica nanoparticle In ethanol for 8h; Reflux; | Synthesis of 6 ,6 a- dih ydr ois oin dol o[2 ,1- a ]-q uin azo line-5,11-dione derivatives 5a-5j General procedure: A mixture of 2-amino-N-(R)-benzamide derivatives(1 mmol), 2-formylbenzoic acid (1 mmol), and 0.1 g SBAPr-SO3H as a catalyst in 7 cm3ethanol were stirred underreflux for 8 h. After reaction completion, the catalyst wasremoved and the product was obtained by recrystallizationfrom ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene Reflux; | Synthesis of quinazolinones (general procedure). General procedure: To a solution of amino amide (0.005 mol) in a xylene-acetic acid (1 : 1) mix-ture (10 mL), 0.005 mol of the corresponding aldehyde (0.01 mol for the synthesis of compound 22) was added and the mixture was re uxed for 3-5 h (TLC control by aldehyde). After keeping under these conditions, the solvent was removed in vacuo, 2% hydrochloric acid was added to the residue, and the precipitate that formed was ltered off . The lter precipitate was washed with 5% soda solution and water and, if necessary, recrystallized from aqueous ethanol. The yields and physicochemical characteristics of 2-aryl quinazolinones 11a-y, 12a-l, 13a,b, 16, 18a,b, and 22a-f are given in Tables 2 and 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With caesium carbonate In water; acetonitrile at 80℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With caesium carbonate In water; acetonitrile at 80℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; | (R)-2-((tert-Butoxycarbonyl)amino)butyric acid (180 mg, 886 mumol), diisopropylethylamine (229 mg, 1.77 mmol),Benzotriazole-1-yl-oxytripyrrolidinylphosphonium hexafluorophosphate (461 mg, 886 mumol) was dissolved in N,N-dimethylformamide (3.00 mL), stirred for 10 minutes and then added.2-amino-N-phenylbenzamide (188 mg, 886 mumol),After the reaction was stirred at room temperature for 1 hour, the solvent was evaporated under reduced pressure.After purification by medium pressure column chromatography, (R)-(1-oxo-1-((2-(phenylamino))Formyl)phenyl)amino)butan-2-yl)carbamic acid tert-butyl ester (180 mg, 453 mumol, yield 51%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 4h; Sealed tube; Green chemistry; | |
With p-toluenesulfonic acid monohydrate; oxygen In water at 110℃; Sealed tube; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 40h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 8h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 4h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With oxygen; toluene-4-sulfonic acid In water at 110℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 16h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 75h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 4h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 85h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 10h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 30h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With oxygen; toluene-4-sulfonic acid In chlorobenzene at 110℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With oxygen; toluene-4-sulfonic acid In water at 110℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper(1+) immobilized onto phenanthroline type ligand-modified magnetic iron oxide nanoparticles-coated graphene oxide nanosheets nanocatalyst In methanol at 20℃; for 20h; | 3.5 General Method for the N-Arylation Reaction General procedure: In a flask containing methanol (2 mL), 2-amino-N-phenylbenzamide(0.5 mmol), phenyl boronic acid (0.5 mmol), andCuPhenMGO catalyst (2 mol%) was added and the reactionmixture was stirred at room temperature. The reactionperformance was followed up by TLC. After the reaction completion, the catalyst was separated by an external magnetand the solvent was evaporated under reduced pressure.The product was obtained by recrystallization from ethanol. |
87% | With triethylamine; copper chloride (I) In methanol at 20℃; for 4h; | General experimental procedure for preparation of 7 and 13a-c by Chan-Evans-Lam coupling General procedure: To a mixture of 1/12a (0.2 mmol), arylboronic acid 6 (0.25 mmol) in methanol was added cuprous chloride (CuCl) (0.03 mmol), and Et3N (0.1 mmol) and stirred at RT for 4h under ambient conditions. After completion of the reaction (monitored by TLC), the reaction mixture was filtered and the filtrate was concentrated and purified by silica gel column chromatography using EtOAc: hexane as eluent to afforded amine N-arylated products 7 (from 1)/13a-c (from 12a) in good yields. |
With triethylamine; copper chloride (I) In methanol at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With 1,4-diaza-bicyclo[2.2.2]octane; dipotassium peroxodisulfate at 160℃; for 2h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With caesium carbonate In acetonitrile at 120℃; for 24h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With N,N,N,N,-tetramethylethylenediamine; di-tert-butyl peroxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 120℃; for 24h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 2,6-di-tert-butyl-4-methyl-phenol; p-toluenesulfonic acid monohydrate; oxygen at 110℃; Sealed tube; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With pyridinium p-toluenesulfonate In tetrahydrofuran at 70℃; for 8h; Inert atmosphere; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With chloro-trimethyl-silane In acetonitrile at 70℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With iodine at 120℃; for 12h; | |
73% | With oxygen; dimethyl sulfoxide; copper(l) chloride at 130℃; for 24h; Green chemistry; | Quinazolinone Derivatives; General Procedure General procedure: A 15 mL pressure tube was charged with 1 (0.3 mmol), DMF (0.1 M), DMSO (1.0 equiv), and CuCl (20 mol%). The reaction mixture was allowedto stir at 130 °C under O2 for about 24 h and allowed to reach rtand then diluted with H2O (5 mL). The aqueous layer was extractedwith EtOAc (3 × 10 mL), and the combined EtOAc layers were washedwith brine (5 mL), dried (MgSO4) and concentrated under reducedpressure. The obtained crude product was purified by column chromatographyby eluting with EtOAc/hexane (1:9) to afford the desiredpure quinazolinone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With toluene-4-sulfonic acid; In ethanol; at 70℃; for 0.5h; | General procedure: The synthesis of spiro indolinone-dihydroquinazolinone 3a-k was accomplished by employing a simple one-pot two components condensationapproach. In first step, an equimolar mixture of isatin derivatives(1) (1.0 mmol) and 2-aminobenzamides (2) (1.0 mmol) was taken into50 mL round-bottom flask. The entire reaction mixture was dissolved in10 mL ethanol and then to catalyze the reaction 10 mol% of p-TsOH was added. The resulting mixture was stirred at 70 C in an oil-bath for 30min. The progress of the reaction was screened by thin layer chromatography(TLC). After completion of the reaction the ethanol solvent was removed under reduced pressure to obtain the crude product. Thereafter,the crude product was taken out with ethyl acetate (20 mL) whichwas washed with brine several times to eliminate the acidic impurities.The organic layer was allowed to dry over anhydrous sodium sulfate(Na2SO4) and concentrated by evaporating ethyl acetate under vacuumto afford the crude product. Finally, the crude was purified by column chromatography on silica gel (60-120 mesh) by employing ethyl acetate/hexane (3:7) as the eluent to obtain pure spiro indolinone dihydroquinazolinone derivatives 3. All the synthesized compounds were characterized based on their spectroscopic data. |
Tags: 4424-17-3 synthesis path| 4424-17-3 SDS| 4424-17-3 COA| 4424-17-3 purity| 4424-17-3 application| 4424-17-3 NMR| 4424-17-3 COA| 4424-17-3 structure
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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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