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Paper | Regular issue | Vol 75, No. 9, 2008, pp.2263-2274
Published online, 8th May, 2008
DOI: 10.3987/COM-08-11396
Synthesis of New 3-Nitroimidazo[1,2-a]pyridine Derivatives by SRN1 Reactions

Rémi Szabo, Maxime D. Crozet, and Patrice Vanelle*

*Universities of Aix-Marseille I, II, and III - CNRS, UMR 6264: Provence Chemistry Laboratory, Radical Pharmaco-Chemistry Team (LPCR), Faculty of Pharmacy, 27 Boulevard Jean Moulin, 13385 Marseille cedex 05, France


6,8-Dibromo-2-chloromethyl-3-nitroimidazo[1,2-a]pyridine was prepared and reacted under experimental conditions of SRN1 reactions with different carbon and sulfur centered nucleophiles to determine the relative reactivities of the different types of electrophile halides. Depending on the nucleophile nature, the chloromethyl group and bromine atom in 8-position were found to be reacting under these experimental conditions. An SRN1 reaction on the pyridine part of the imidazo[1,2-a]pyridine is described for the first time.