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Paper | Regular issue | Vol 36, No. 7, 1993, pp.1541-1551
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6329
SRN1 Reactions in Imidazo[1,2-a][1,8]naphthyridine Series

Patrice Vanelle,* Saïd Ghezali, José Maldonado, Olivier Chavignon, Alain Gueiffier, Jean-Claude Teulade, and Michel P. Crozet*

*Radicaux Libres et Synthèse, CNRS URA 1412, Université e’Aix-Marseille III, Faculté des Sciences et Techniques de St.-Jérôme, Avenue Escardrille Normandie-Niemen BP 562,13397 Marseille Cedex 20, France

Abstract

8-Chloromethyl-2,4-dimethyl-9-nitroimidazo[1,2-a][1,8]naphthyridine was synthesized as reductive alkylating agent and its reactivity with 2-nitropropane anion was investigated. The SRN1 mechanism of the C-alkylation was confirmed by the inhibitory effects of p-dinitrobenzene, molecular oxygen and TEMPO. Extension of this SRN1 reaction to various nitronate anions leads after nitrous acid elimination to a new class of imidazo[1,2-a][1,8]naphthyridine derivatives bearing a trisubstituted double bond at the 8 position.