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Paper | Regular issue | Vol 71, No. 12, 2007, pp.2681-2688
Published online, 31st August, 2007
DOI: 10.3987/COM-07-11162
Synthesis of 8-Substituted 12-Methyl-12H-imidazo[4’,5’: 2,3][1,4]diazepino[6,7,1-jk]carbazoles

Kayed A. Abu Safieh, Fouad H. Darras, Mikdad T. Ayoub, Mustafa M. El-Abadelah, Salim S. Sabri, and Wolfgang Voelter*

*Interfakultaeres Institut fuer Biochemie, Universitaet Tuebingen, Hoppe-Seyler Strasse 4, D-72076 Tuebingen, Germany

Abstract

A synthesis of model 8-substituted-12-methyl-12H-imidazo[4’, 5’: 2,3][1,4]-diazepino[6,7,1-jk]carbazoles (10a-c), based on the classical Bischler-Napieralski method, is described. Thus interaction of carbazole with 5-chloro-1-methyl-4-nitro-1H-imidazole (in the presence of sodium hydride) produced the corresponding 9-(1-methyl-4-nitro-1H-imidazole-5-yl)-9H-carbazole (7). Chemical reduction of the nitro group of 7 into the respective amino derivative 8, and subsequent acylation of the resulting amino group furnished the respective amides 9a-c. Cyclocondensation of the latter amides, using polyphosphoric acid under Bischler-Napieralski reaction conditions, delivered the target compounds 10a-c. The structures of these new pentacyclic heterocycles were supported by IR, MS, and NMR spectral data.