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Paper | Regular issue | Vol 36, No. 1, 1993, pp.45-54
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6028
■ Synthesis and SRN1 Reaction of the First Quinone-Oxazole Bioreductive Alkylating Agent

Michel P. Crozet,* Jean-François Sabuco, Isabelle Tamburlin, Michel Barreau, Luc Giraud, and Patrice Vanelle

*Radicaux Libres et Synthèse, CNRS URA 1412, Faculté des Sciences et Techniques de Saint-Jérôme, P.O. Box 562, Université de Droit, d’Economie et des Sciences d’Aix-Marseille, 13397 Marseille Cedex 13, France

Abstract

2-(2-Chloromethyloxazol-5-yl)-3,5,6-trimethyl-1,4-benzoquinone, the first compound of a new quinone-heterocyclic class of bioreductive alkylating agent, was prepared from trimethylhydroquinone in 8 steps and reacted by SRN1 reaction with lithium salt of 2-nitropropane. The C-alkylation derivative showing its ability to react as one electron bioreductive alkylating agent was obtained in 88% yield.