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Paper | Regular issue | Vol 43, No. 6, 1996, pp.1229-1241
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7440
Preparation of Aza-Analogs of Aplysinopsins and Zwitterionic by Reactions of Heterocumulenes in Naphthyridine's Series

Grégory Delmas, Patricia Deplat, Jean Michel Chezal, Olivier Chavignon,* Alain Gueiffier, Yves Blache, Jean Louis Chabard, Gérard Dauphin, and Jean Claude Teulade

*Département d'Analyse Structurale et de Pharmacologie, Laboratoire de Chimie Organique, Faculté de Pharmacie, 28 Pl. H. Dunant, B.P. 38, 63001 Clermont-Ferrand Cedex 1, France

Abstract

Imidazo[1,2-a][1,8]naphthyridines (9a,b) having the carbodiimide moiety on the position 1 lead to (Z)-aza-aplysinopsins (10a,b) by solid suported reaction on neutral alumina. By flash chromatography these heterocumulenes are stereosapecifically converted to the corresponding methoxyimidazol-4-ones (11a,b) in good yields. In contrast, tandem aza-Wittig-cyclization reaction of imidazo[1,2-a][1,8]naphthyridine (13) having iminophosphorane moiety on the position 2 gives zwitterionic compounds (14a,b,15) by N-annulation under thermal conditions.