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Paper | Regular issue | Vol 51, No. 10, 1999, pp.2335-2342
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8586
New Synthesis of Benzo[a]phenazines Based on Acid Promoted Ring Opening of the Benzotriazole Moiety

Alan R. Katritzky,* Abd El Rachman Ferwanah, Yasuhisa Matsukawa, Peter J. Steel, and Sergey N. Denisenko

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, U.S.A.

Abstract

Syntheses of benzo[a]phenazines (6a-d) have been accomplished based on an acid promoted tandem benzotriazole ring-opening / ammonia extrusion procedure. Compounds (6a-d) are thus accessible directly from 3-(benzotriazol-1-yl)-1,4-diaryl-1-buten-4-ols (3a-d) in one-pot reaction sequences or from the intermediate 3,4-dihydronaphthalenes (4a-c). This constitutes a new type of benzotriazole ring transformation.