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Selective Access to 4-Substituted 2-Aminothiazoles and 4-Substituted 5-Thiocyano-2-aminothiazoles from Vinyl Azides and Potassium Thiocyanate Switched by Palladium and Iron Catalysts

Binhui Chen, Shanshan Guo, Xiao Guo, Guolin Zhang* and Yongping Yu*

*Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. China, Email: guolinzhangzju.edu.cn, yyuzju.edu.cn

B. Chen, S. Guo, X. Guo, G. Zhang, Y. Yu, Org. Lett., 2015, 17, 4698-4701.

DOI: 10.1021/acs.orglett.5b02152 (free Supporting Information)


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Abstract

Palladium(II) acetate catalyzes a highly selective construction of 4-substituted 2-aminothiazoles from vinyl azides and potassium thiocyanate, whereas iron(III) bromide promotes the formation of 4-substituted 5-thiocyano-2-aminothiazoles. Use of readily available starting materials, high selectivity, as well as mild reaction conditions make these practical methods particularly attractive.

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Key Words

thiazoles


ID: J54-Y2015