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

Author:
Xiang, Dexuan, Xin, Xiaoqing, Liu, Xu, Zhang, Rui, Yang, Jiming, Dong, Dewen
Source:
Organic letters 2012 v.14 no.2 pp. 644-647
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, hydroxylamine, organic compounds, potassium hydroxide, regioselectivity
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.
Agid:
5784514