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Synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides via [[3+3]-1] pathway

Abstract

A novel and practical protocol for the synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides in excellent yields under mild conditions is described. The transformation proceeds via an unusual [[3+3]-1] pathway, which involves a formal [3+3] cascade cyclization followed by a spontaneous ring-contraction/sulfur extrusion reaction from 4H-1,3,4-thiadiazine intermediates.

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Article information


Submitted
03 Feb 2020
Accepted
24 Mar 2020
First published
24 Mar 2020

Org. Biomol. Chem., 2020, Accepted Manuscript
Article type
Paper

Synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides via [[3+3]-1] pathway

B. Cheng, B. Bao, W. Xu, Y. Li, H. Li, X. Zhang, Y. Li, T. Wang and H. Zhai, Org. Biomol. Chem., 2020, Accepted Manuscript , DOI: 10.1039/D0OB00224K

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