In continuation of our research program to develop original synthetic methods using TDAE methodology on nitroheterocyclic substrates, we were able to generate for the first time a stable carbanion in position 2 of the 5-nitroimidazole scaffold. Starting from a 2-chloromethyl-4-phenylsulfonylmethyl-5-nitroimidazole intermediate, prepared by the vicarious nucleophilic substitution of hydrogen (VNS) reaction, we selectively introduced a N-tosylbenzylimine moiety at position 2 without reducing the sulfone at position 4, leading to the formation of N-[1-(2-chlorophenyl)-2-{1-methyl-5-nitro-4-[(phenylsulfonyl)methyl]-1H-imidazol-2-yl}ethyl]-4-methylbenzenesulfonamide in 47% yield. This new synthetic method using TDAE should allow access to new 2-substituted 5-nitroimidazole derivatives with various electrophiles such as carbonyls and other N-tosylbenzylimines.

中文翻译：

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N-[1-(2-氯苯基)-2-{1-甲基-5-硝基-4-[(苯磺酰基)甲基]-1H-咪唑-2-基}乙基]-4-甲基苯磺酰胺

在继续我们使用 TDAE 方法对硝基杂环底物开发原始合成方法的研究计划中，我们首次能够在 5-硝基咪唑支架的 2 位生成稳定的负碳离子。从通过氢的替代亲核取代 (VNS) 反应制备的 2-氯甲基-4-苯磺酰基甲基-5-硝基咪唑中间体开始，我们选择性地在 2 位引入 N-甲苯磺酰基苄亚胺部分而不还原 4 位的砜，导致N-[1-(2-氯苯基)-2-{1-甲基-5-硝基-4-[(苯磺酰基)甲基]-1H-咪唑-2-基}乙基]-4-甲基苯磺酰胺在47中的形成％ 屈服。