N. Egorova, T. Artamonova, A. Hrabálek
Sep 1, 2005
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0
Influential Citations
5
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Journal
Russian Journal of Organic Chemistry
Abstract
Wide application of tetrazoles in the synthesis of new medical agents for various purposes [1–7] stimulated extensive search for simple and effective procedures for functionalization of these compounds. While continuing our studies on 1-aryltetrazole-5-thiones as readily accessible synthons for the preparation of functionally substituted tetrazoles, we examined the reactivity of 5-methylsulfinyl-1-(4-nitrophenyl)tetrazole with respect to various nitrogen-centered nucleophiles. Initial 5-methylsulfinyl-1-(4-nitrophenyl)tetrazole (I) was synthesized by oxidation of 5-methylsulfanyl-1(4-nitrophenyl)tetrazole with 35% hydrogen peroxide in acetic acid at 70°C (Scheme 1). Under these conditions, compound I was formed in almost quantitative yield. The rate of oxidation considerably increases under microwave irradiation, while the yield of tetrazole I remains almost unchanged.