Diversity-Oriented Synthesis of 1,2,4-Triazoles, 1,3,4-Thiadiazoles, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

Zeyang Wei, Qi Zhang, Meng Tang*, Siyu Zhang and Qian Zhang

*School of Pharmacy, Lanzhou University, Lanzhou 730000, P. R. China, Email: tangmenglzu.edu.cn

Z. Wei, Q. Zhang, M. Tang, S. Zhang, Q. Zhang, Org. Lett., 2021, 23, 4420-4425.

DOI: 10.1021/acs.orglett.1c01379

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Abstract

N-Tosylhydrazones can be used as substrates for diversity-oriented synthesis of 1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4-selenadiazoles with NH₂CN, KOCN, KSCN, and KSeCN as odorless reaction partners. Reactions in the presence of NCS include an in situ formation of N-tosylhydrazonoyl chlorides.

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proposed mechanisms

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Key Words

1,2,4-Triazoles, 1,3,4-Thiadiazoles

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ID: J54-Y2021