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

Reaction equation

[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

Participants

Reactant 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

Product 1

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

Procedure

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%).