Regioselective Synthesis of Isoxazoles from Propargylic Alcohols via In‐situ‐formed α‐Iodo Enones/Enals

Author:

Yang Hong1,Chen Jiaming2,He Shuai2,Wu Lijuan2,Zhou Min2,Yang Wenfeng3,Cai Jiaming2,Wang Zhuowen2,Wang Jianlun2,Wang Xiaoyang2,yin yan4,Wang Zhuwen2

Affiliation:

1. Shanghai Institute of Technology Department of Chemical Environmantal Engineering CHINA

2. Shanghai Institute of Technology Department of Chemical and Environmental Engineering CHINA

3. Shanghai Institute of Technology Department of chemical and environmentla engireeing CHINA

4. Shanghai Institute of Technology School of Chemical and Envrionmental Engineering 100 haiquan Rd. 201418 Shanghai CHINA

Abstract

A regioselective synthesis of isoxazoles with propargyl alcohols, N‐iodosuccinimide (NIS), and N‐tert‐butyl hydroxylamine hydrochloride (t‐BuNHOH•HCl) as the reaction substrates is reported. Reaction scope investigations indicated that primary and secondary propargyl alcohols underwent this transformation smoothly to afford 5‐, 3‐, and 3,5‐substituted isoxazoles in moderate to good yields. The reaction most likely involves an electrophilic‐intercepted Meyer–Schuster rearrangement of the propargyl alcohol, followed by intermolecular cyclocondensation of N‐tert‐butyl hydroxylamine and in‐situ‐formed α‐iodo enones/enals. This one‐pot method is regioselective and easy to perform, making it a valuable method for the construction of isoxazoles. Finally, its application was explored through the synthesis of valdecoxib.

Publisher

Wiley

Subject

Organic Chemistry

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