Diazaindenes (azaindoles). Part VI. Preparation and some properties of 1,7-diazaindene 7-oxide and 6,7,8,9-tetrahydro-γ-carboline 2-oxide

Abstract

Treatment of the N-acetyl derivatives of 1,7-diazaindene and 6,7,8,9-tetrahydro-γ-carboline with m-chloroperoxybenzoic acid gave the 7-oxide (6) and the 2-oxide (13), respectively. The reaction of the N-oxide (13) with acetic anhydride yielded 6,7,8,9-tetrahydro-γ-carbolin-1(2H)-one (24), and the 7-oxide (6) gave 1,7-diazainden-6(7H)-one (26). 1-Chloro-6,7,8,9-tetrahydro-γ-carboline (14) was obtained directly from the N-oxide (13), but the 7-oxide (6) gave 4-chloro-1,7-diazaindene (8); the chlorine atom in (8) was not easily replaced by nucleophiles. The tetrahydro-γ-carboline N-oxide (13) was converted into 1-cyano-(16) and 1-anilino-tetrahydro-γ-carboline (18).