Methanol → 1-benzyl-4-(3-methylphenyl)carbamyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

반응식

[O:1]=[O+][O-].[CH2:4]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)C2[CH2:20][CH2:21][N:22]([C:24](=[O:33])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=3)[CH2:23][C:12]1=2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CSC.[CH3:37][OH:38]>>[CH2:4]([N:11]1[C:19]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:37](=[O:38])[CH2:20][CH2:21][N:22]([C:24](=[O:33])[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[CH2:23][C:12]1=[O:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

반응물 4

HCID 887Methanol

HCID 1068Dimethyl Sulfide

HCID 24823Ozone

HCID 187881639-benzyl-2-(3-methylphenyl)carbamyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

생성물 1

HCID 187881991-benzyl-4-(3-methylphenyl)carbamyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

실험 절차

Ozone was bubbled through a solution of 9-benzyl-2-(3-methylphenyl)carbamyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (2.98 g, 7.54 mmol) in methanol (40 ml) at -78° C. until a blue colour persisted. Nitrogen was then bubbled through the solution until clear, followed by the addition of dimethyl sulphide (5.0 ml, 68.1 mmol). The solution was allowed to warm to room temperature and stirring continued for a further 2 hours, followed by evaporation to dryness. The crude product was purified by chromatography on silica gel with ethyl acetate-hexane (3:2) as eluant. (2.0 g, 62%).