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Paper | Regular issue | Vol 63, No. 8, 2004, pp.1855-1873
Published online, 9th July, 2004
DOI: 10.3987/COM-04-10134
Allylic Dehydration, Retro-Pinacol, Pinacol-like and Enamide Reactions: Synthesis of New Isoquinolines

Rufine Akué-Gédu, Anne Bourry, Fabrice Camus, Bernadette Norberg, François Durant, Daniel Couturier, Marc DeBacker, and Benoît Rigo*

*Group de Recherche sur l’Inhibition de la Prolifération Cellulaire (EA 2692), Hautes Etudes d’Ingénieurs, 13 rue de Toul, 59046 Lille, France

Abstract

Depending upon the conditions, heating of 1,10a-dihydro-2H,5H-pyrrolo[1,2-b]isoquinoline-3,10-diones in polyphosphoric or hydrochloric acid gives rise to hydride transfer and oxidative processes. Mono or dienyl lactams, or mixtures of dimers and acids or hydroxyacids of the isoquinoline series were thus formed. Procedures leading specifically to each of these products have been found.