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Paper | Special issue | Vol 37, No. 3, 1994, pp.1549-1559
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S101
Polycondensed Nitrogen Heterocycles. Part 26. Aminopyrrolo[1,2-f]phenanthridines by Decomposition and Cyclization of 2-Aryl-1-(3-azidophenyl)pyrroles

Anna Maria Almerico, Girolamo Cirrincione, Patrizia Diana, Stefania Grimaudo, Gaetano Dattolo, Enrico Aiello,* Francesco Mingoia, and Paola Barraja

*Instituto Farmacochimico, Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy


Acid catalyzed decomposition of 1-(3-azidophenyl)pyrroles (8a-d) afforded the 6-amino- and 8-aminopyrrolo[1,2-f]phenanthridines of type (11) and (12) through cyclization of the intermediate protosolvated arylnitrenium ions (9). In the case of azide (8a,b) intermolecular side-reactions led also to the hydroxyphenyl derivatives (10).