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Paper | Regular issue | Vol 51, No. 5, 1999, pp.1003-1014
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8466
Reactivity of Heterocyclic Enaminones: Regioselective Synthesis of Some Pyridobenzodiazepines and Imidazopyridines

Yves Blache,* Mohammed Hichour, Genoveffa Di Blasi, Jean-Michel Chezal, Henri Viols, Olivier Chavignon, Jean-Claude Teulade, and Jean-Pierre Chapat

*E. A. 2414 Pharmacochimie et Biomolécules, Laboratoire de Chimie Organique Pharmaceutique, Université Montpellier I, 15 Avenue Charles Flahault, 34060 Montpellier, France

Abstract

Reactivity of enaminones derived from various diaminopyridines toward electrophilic carbons (imines, carbodiimides, isocyanates) is reported. The reactions leading to diazepinic or imidazolic ring systems are shown to be dependent of the electrophilic species as well as of the position of the nitrogen atom in the heterocyclic ring.