The Journal of Organic Chemistry 2017-05-12

Synthesis of 5-Amino and 3,5-Diamino Substituted 1,2,4-Thiadiazoles by I2-Mediated Oxidative N–S Bond Formation

Bingnan Wang, Yinggao Meng, Yiming Zhou, Linning Ren, Jie Wu, Wenquan Yu, Junbiao Chang

Index: 10.1021/acs.joc.7b00814

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Abstract

An oxidative N–S bond formation reaction has been established for 1,2,4-thiadiazole synthesis employing molecular iodine as the sole oxidant. The features of the present reaction include no use of transition metals, mild reaction conditions, simple operation, and short reaction time. This versatile synthetic approach is broadly applicable to a variety of imidoyl and guanyl thiourea substrates to produce 5-amino and 3,5-diamino substituted 1,2,4-thiadiazole derivatives, respectively, in an efficient and scalable fashion.