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Paper | Regular issue | Vol 38, No. 11, 1994, pp.2401-2405
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6815
Reactions of 16-Nitroindolenines of the Vincadifformine Type

Guy Lewin,* Yves Rolland, Corinne Schaeffer, and Jacques Poisson

*Laboratoire de Pharmaceutiques, Faculté de Pharmacie, Centre d‘Etudes et de Recherch sur le Medicament de Normandie, 1, ue Vaubénard, 14032 Caen Cedex, France

Abstract

The reactivity of 16-nitroindolenine (4), a byproduct of the aromatic nitration of vincadifformine (1), has been studied. In TFA 4 yielded 10-nitrovincadifformine (3) whereas acid hydrolytic treatment led to the tetracyclic oxindole structure (8) by cleavage of the 2-16 bond. Reduction of 4 (SnCl2 or hydrogenolysis) allowed recovery of 1 in good yield.