Beta-Nitrostyrene → (Rac)-3-phenyl-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol-6-one

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Reaction Conditions

Reaction Steps

In a manner similar to that described for the preparation of methyl 3-(nitroethyl)-indole-4-carboxylate D above, methyl indole4-carboxylate (85 mg, 0.49 mmol) and nitrostyrene (80 mg, 0.54 mmol) were heated at 160° C. in a sealed tube for 12 h. The product was isolated by silica gel chromatography as a brown oil, 132 mg (83%). The intermediate nitro alkane was reduced/cyclized as described to give (rac)-3-phenyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one as a white solid, 51.4 mg (48%, after chromatography and recrystallization). mp 201-203° C.; 1H NMR (300 MHz, d6-DMSO) δ3.73 (m, 2H), 4.42 (m, 1H), 7.28 (br m, 8H), 7.64 (d, 1H, J=7.9 Hz), 7.77 (d, 1H, J=7.9 Hz), 11.32 (br s, 1H); HRMS (FAB, MH+) Calcd for C17H15N2O: 263.1184, Found: 263.1180; Anal. (C17H14N2O.0.25 H2O) C, H, N.

Provenance & Evidence