One-Pot Synthesis of 5-Acyl-1,2,3-Thiadiazoles from Enaminones, Tosylhydrazine, and Elemental Sulfur under Transition-Metal-Free Conditions
Zan Yang, Yemei Liang, An Li, Kun Liu*, Lijun Li, Tao Yang* and Congshan Zhou*
*College of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China, Email: liukun328126.com, yangtaozcs126.com, zhoucongsh126.com
Z. Yang, Y. Liang, A. Li, K. Liu, L. Li, T. Yang, C. Zhou, J. Org. Chem., 2019, 84, 16262-16267.
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The combination of I2 with dimethyl sulfoxide mediates a cross-coupling cyclization of enaminones, tosylhydrazine, and elemental sulfur for the synthesis of 5-acyl-1,2,3-thiadiazoles in very good yields under transition-metal-free conditions. This strategy is operationally simple and compatible with a wide range of functional groups.
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1,2,3-thiadiazoles, iodine, multicomponent reactions