Iron(III) Chloride Catalyzed Nucleophilic Substitution of Tertiary Propargylic Alcohols and Synthesis of Iodo-3H-Pyrazoles

Xiao-Tao Liu*, Zong-Cang Ding, Lu-Chuan Ju, Zhao-Ning Tang, Feng Wu, Zhuang-Ping Zhan*

*Huaian Wanbang Aromatic Chemicals Industry Co., Ltd., Huaian 223300, Jiangsu; Department of Chemistry, Xiamen University, Xiamen 361005, Fujian, P. R. of China , Email: xiaotao.liuwxintl.com, zpzhanxmu.edu.cn

X.-T. Liu, Z.-C. Ding, L-C. Ju, Z.-N. Tang, F. Wu, Z.-P. Zhan, Synlett, 2017, 28, 620-624.

DOI: 10.1055/s-0036-1588362

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Abstract

FeCl₃ mediates a propargylic substitution of tertiary propargylic alcohols with p-toluenesulfonyl hydrazide. A subsequent cyclization under mild conditions in the presence of iodine enables an efficient and rapid synthesis of iodo-3H-pyrazoles with a wide substrate scope and in high yields.

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Key Words

propargylic alcohols, tosyl hydrazide, hydrazides, cyclization, iodination, 3H-pyrazoles

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ID: J60-Y2017