苯丙炔醛

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4.8 g (0.030 mole) of 3-diazooxindole is suspended in 350 ml of benzene and 3.9 g (0.030 mole) of phenylpropargylaldehyde added. The reaction mixture is refluxed under nitrogen for 48 hours. The reaction mixture is refluxed under nitrogen for 48 hours

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 10 mL of a chloroform solution containing 500 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one and 1940 mg of phenylpropargylaldehyde, 100 mg of acetic acid were added, and stirred at room temperature for 2 hours. To the reaction mixture, 526 mg of sodium triacetoxyborohydride was added, and stirred for 14 hours. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=10:1], to give 0.27 g of 7-methoxy-1-(2-(4-(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)quinoxalin-2(1H)-one as a brown oil and 0.23 g of 1-(2-(4-(bis(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a brown oil. were added stirred for 14 hours the organic layer was separated The organic layer was washed with aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate the solvent was removed under reduced pressure The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=10:1]

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 10 mL of a chloroform solution containing 404 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one and 180 mg of phenylpropargylaldehyde, 80 μL of acetic acid were added, and stirred at room temperature for 1 hour. To the reaction mixture, 474 mg of sodium triacetoxyborohydride was added, and stirred overnight. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=2:1], to give 224 mg of 7-fluoro-1-(2-(4-(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)quinoxalin-2(1H)-one as brown solid and 158 mg of 1-(2-(4-(bis(3-phenyl-2-propyn-1-yl)amino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one as yellow oil. were added stirred overnight the organic layer was separated The organic layer was washed with aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate the solvent was removed under reduced pressure The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=2:1]

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 5-hexenimidamide hydrochloride (P4, 500 mg), 3-phenyl-2-propynal (398 mg), and sodium carbonate (786 mg) in acetonitrile (15 mL) was irradiated in a microwave synthesizer at 120° C. for 40 min and then allowed to cool. The solution was filtered and evaporated in vacuo. The residue was dissolved in dichloromethane and the organic layer was washed with H2O, dried over Na2SO4, filtered and evaporated in vacuo. The crude was purified by column chromatography (eluting with ciclohexane/ethyl acetate 9/1) to give 142 mg of the title compound. was irradiated in a microwave synthesizer at 120° C. for 40 min to cool The solution was filtered evaporated in vacuo The residue was dissolved in dichloromethane the organic layer was washed with H2O dried over Na2SO4 filtered evaporated in vacuo The crude was purified by column chromatography (eluting with ciclohexane/ethyl acetate 9/1)

反应条件: temp:22.01; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 10 mL of a chloroform solution containing 500 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one and 1940 mg of phenylpropargylaldehyde, 100 mg of acetic acid were added, and stirred at room temperature for 2 hours. To the reaction mixture, 526 mg of sodium triacetoxyborohydride was added, and stirred for 14 hours. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=10:1], to give 0.27 g of 7-methoxy-1-(2-(4-(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)quinoxalin-2(1H)-one as a brown oil and 0.23 g of 1-(2-(4-(bis(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a brown oil. were added stirred for 14 hours the organic layer was separated The organic layer was washed with aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate the solvent was removed under reduced pressure The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=10:1]

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 10 mL of a chloroform solution containing 404 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one and 180 mg of phenylpropargylaldehyde, 80 μL of acetic acid were added, and stirred at room temperature for 1 hour. To the reaction mixture, 474 mg of sodium triacetoxyborohydride was added, and stirred overnight. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=2:1], to give 224 mg of 7-fluoro-1-(2-(4-(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)quinoxalin-2(1H)-one as brown solid and 158 mg of 1-(2-(4-(bis(3-phenyl-2-propyn-1-yl)amino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one as yellow oil. were added stirred overnight the organic layer was separated The organic layer was washed with aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate the solvent was removed under reduced pressure The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=2:1]

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 5-hexenimidamide hydrochloride (P4, 500 mg), 3-phenyl-2-propynal (398 mg), and sodium carbonate (786 mg) in acetonitrile (15 mL) was irradiated in a microwave synthesizer at 120° C. for 40 min and then allowed to cool. The solution was filtered and evaporated in vacuo. The residue was dissolved in dichloromethane and the organic layer was washed with H2O, dried over Na2SO4, filtered and evaporated in vacuo. The crude was purified by column chromatography (eluting with ciclohexane/ethyl acetate 9/1) to give 142 mg of the title compound. was irradiated in a microwave synthesizer at 120° C. for 40 min to cool The solution was filtered evaporated in vacuo The residue was dissolved in dichloromethane the organic layer was washed with H2O dried over Na2SO4 filtered evaporated in vacuo The crude was purified by column chromatography (eluting with ciclohexane/ethyl acetate 9/1)

实验步骤: 投料: 向三口瓶中依次加入1.0gSM1(1.0eq),DMSO(7V),0.43gDABCO(0.5eq)室温保温反应2h中控，反应完全，体系加入15VH2O，加入8VEA萃取三次，有机相加入10V洗涤一次，饱和氯化钠洗涤一次，有机相干燥，浓缩干，过柱子

实验步骤: 投料: 向双口瓶中依次加入5gSM1(1.0eq)，50mlDMSO，2.15gDABCO(0.5eq)，滴加3.96gSM2(1.2eq)，20~25℃保温搅拌2h，取样gcms监测原料反应完全，体系加入(10V)H2O，(5V)EA重复萃取四次，有机相合并加入(15V)H2O洗涤四次，有机相干燥浓缩得6.1g黄色液体，送样cim100400-90-109-o（GCMS）

实验步骤: 投料: 向100ml三口瓶中依次加入5gSM1(1.0eq)，50mlDMSO，2.15gDABCO(0.5eq)，滴加3.96gSM2(1.2eq)，20~25℃保温搅拌2h，取样gcms监测原料反应完全，体系加入(10V)H2O，(5V)EA重复萃取四次，有机相合并加入(15V)H2O洗涤四次，有机相干燥浓缩得5.9g黄色液体，送样cim100400-90-105-o（GCMS）

实验步骤: 投料: 向双口瓶中依次加入1gSM1(1.0eq)，10mlDMSO，0.43gDABCO(0.5eq)，滴加0.8gSM2(1.2eq)，20~25℃保温搅拌2h，取样gcms监测原料反应完全，体系加入(10V)H2O，(5V)EA重复萃取四次，有机相合并加入(15V)H2O洗涤四次，有机相干燥浓缩得1.12g黄色液体，送样cim100400-90-103-o（GCMS）