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Efficient regioselective synthesis of 4‐ and 5‐substituted isoxazoles under thermal and microwave conditions
Author(s) -
Lasri Jamal,
Mukhopadhyay Suman,
Charmier M. Adflia Januário,
Charmier M. Adflia Januário
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450521
Subject(s) - regioselectivity , isoxazole , chemistry , cycloaddition , nitrile , microwave irradiation , microwave , organic chemistry , catalysis , physics , quantum mechanics
The [2+3] cycloaddition reaction between nitrile oxides 2 and the captodative olefins 1 or the methyl crotonate derivatives 4 is regioselective and leads to the formation of the 5‐substituted amino‐isoxazole 3 or the 4‐substituted methoxycarbonyl‐isoxazole 5 derivatives, respectively. All these reactions are greatly accelerated by microwave irradiation without changing their regioselectivity with respect to the thermal conditions.