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Paper | Regular issue | Vol 48, No. 4, 1998, pp.687-693
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8070
Rearrangement of an N-Aryl-2-vinyltetrahydro-4-oxoquinoline to an Acridine Derivative

Claire Clémencin-Le Guillou, Sylviane Giorgi-Renault,* Jean-Charles Quirion,* and Henri-Philippe Husson

*Laboratoire de Chimie Thérapeutique associé au C.N.R.S., Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes, 4, avenue de l'Observatoire, 75270 Pairs Cedex 06, France

Abstract

Acridine (4) has been obtained by acidic rearrangement of N-aryl-2-vinyltetrahydro-4-oxoquinoline (2). The mechanism involved a retro-Michael process followed by the attack of the electron rich aromatic ring onto the keto group.