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Paper | Regular issue | Vol 53, No. 4, 2000, pp.905-916
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8837
Reactivity of Heterocyclic Enaminones: Regioselective Synthesis of Polyfused Indolones

Yves Blache,* Véronique Benezech, Jean-Michel Chezal, Pierre Boule, Henri Viols, Olivier Chavignon, Jean-Claude Teulade, and Jean-Pierre Chapat

*Laboratoire de Chimie Organique Pharmaceutique, E. A. 2414, 15 Avenue Charles Flahault, Faculté de Pharmacie, 34060 Montpellier, France

Abstract

Photocyclization of heterocyclic enaminones to give partial hydrogenated derivatives of indolo[2,3-c]quinoline, pyrido[2,3-c]carbazole, and pyrido[4,3-a]carbazole is described. In addition, 3-[(5’-quinolinyl)- benzylamino]cyclohex-2-en-1-one and 3-[(8’-quinolinyl) benzylamino]cyclohex-2-en-1-one undergo C-N bond cleavages and a benzyl migration on the C-6 and C-7 positions respectively.