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.

DOI: 10.1021/acs.joc.9b02866

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Abstract

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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Key Words

1,2,3-thiadiazoles, iodine, multicomponent reactions

ID: J42-Y2019

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*

Zan Yang, Yemei Liang, An Li, Kun Liu, Lijun Li, Tao Yang and Congshan Zhou*