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January 3, 2012Organic Letters

Regioselective Synthesis of 3-Arylamino- and 5-Arylaminoisoxazoles from Enaminones

Dexuan Xiang Xiaoqing Xin Xu Liu Rui Zhang Jiming Yang Dewen Dong

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Abstract

A highly regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles from enaminones based on reaction condition selection is reported. 3-Arylaminoisoxazoles were produced by treating enaminones with aqueous hydroxylamine in DMF at 100 °C, whereas 5-arylaminoisoxazoles were synthesized by subjecting enaminones to aqueous hydroxylamine in the presence of KOH and TBAB in water under reflux. A mechanism for the regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles is proposed.

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Cite This Study

Xiang et al. (2012) studied this question.

synapsesocial.com/papers/6a99e39d6f891be7b24d3003 https://doi.org/10.1021/ol203282h

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