Dimethylformamide → HCID 9796204、化合物

反応式

[H-].[Na+].[CH2:3]=[C:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][N:5]1[C:19]([CH:21]1[CH2:23][CH2:22]1)=[O:20].CN(C=[O:28])C>>[CH:21]1([C:19]([N:5]2[CH2:6][C:7]3[C:8](=[O:28])[C:9]4[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=4[NH:15][C:16]=3[C:4]2=[CH2:3])=[O:20])[CH2:22][CH2:23]1

参加物

反応物 3

HCID 6228Dimethylformamide

HCID 24758Sodium hydride2 回

HCID 18328985HCID 18328985、化合物

生成物 1

HCID 9796204HCID 9796204、化合物収率 38%

実験手順

NaH (1.2 eq; 60% suspension in oil) is added to a solution of 1-methylene-2-cyclopropylcarbonyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (500 mg; 1.7 mmol) in DMF (5 ml). The mixture is stirred under an oxygen atmosphere for 48 hours, further NaH (1.1 eq) is then added and stirring is continued overnight. The DMF is then distilled off under reduced pressure. The crude product is taken up in water and then filtered off. Saturated NH4Cl solution is added to the aqueous phase. The mixture is stirred for 30 minutes. The precipitate is filtered off and then washed successively with water, an MeOH/CH2Cl2 mixture (10/90), acetone and then ethyl acetate. After drying, 2-cyclopropylcarbonyl-7-methoxy-3-methylene-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline is obtained (yield=38%).