Facile One-Pot Preparation of 5-Substituted 4-Iodo-1-tosylpyrazoles from N-Propargyl-N′-tosylhydrazines through Iodocyclization

Abstract

Treatment of N-propargyl-N′-tosylhydrazines with molecular iodine (I₂) in the presence of NaHCO₃ under warming conditions gave efficiently the corresponding 5-substituted 4-iodo-1-tosylpyrazoles in good to moderate yields. In addition, the same reaction in the presence of acetic acid generated the corresponding 5-aryl-4-iodopyrazoles in moderate yields. The reactions are simple and efficient transition-metal-free methods for the preparation of 5-substituted 4-iodo­pyrazole unit.

Key words

4-iodopyrazole - molecular iodine - iodocyclization - N-propargyl-N′-tosylhydrazine - transition-metal-free

Publication History

Received: 18 January 2022

Accepted after revision: 15 February 2022

Article published online:
28 March 2022

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