SYNTHESIS AND S(RN)1 REACTIONS IN 5-NITRO THIAZOLE SERIES

A new heterocyclic reductive alkylating agent, the 2-methyl-4-chlorome thyl-5-nitrothiazole, has been synthesized and could react with the 2- nitropropane anion as nucleophile, to give the 2-methyl-4-(2-methylpro penyl)-5-nitrothiazole as the major product. The reaction was shown to proceed by the S(RN)1 mechanism which was confirmed by the classical criteria for S(RN)1 reaction: the leaving group effect, the electronwi thdrawing group effect and classical inhibition experiments by dioxyge n, p-dinitrobenzene, cupric chloride or di-tert-butylnitroxide. This r eaction has been extended to nitrocyclopentane and nitrocyclohexane an ions with lower yields. (C) 1997 Elsevier Science Ltd.