Selective ortho methylation of nitroheteroaryls by vicarious nucleophilic substitution

…, C Goldstein, C Affouard, R Jensen…

Index: Achmatowicz, Michal; Thiel, Oliver R.; Gorins, Gilles; Goldstein, Corinne; Affouard, Caroline; Jensen, Randy; Larsen, Robert D. Journal of Organic Chemistry, 2008 , vol. 73, # 17 p. 6793 - 6799

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Citation Number: 8

Abstract

An efficient and scalable three-step one-pot approach to 6-methyl-5-nitroisoquinoline (1) from inexpensive 5-nitroisoquinoline, utilizing the vicarious nucleophilic substitution (VNS) as a key step, is described. The optimized reaction conditions can be applied to a limited number of other aromatic and heteroaromatic nitro compounds. Attempts to understand the observed selectivity in the VNS step led to the discovery of two new reaction pathways ...