One-Pot Three-Component Heteroannulation of β-Oxo Dithioesters, Amines and Hydroxylamine: Regioselective, Facile and Straightforward Entry to 5-Substituted 3-Aminoisoxazoles

Samai, Subhasis ; Chanda, Tanmoy ; Ila, Hiriyakkanavar ; Singh, Maya Shankar (2013) One-Pot Three-Component Heteroannulation of β-Oxo Dithioesters, Amines and Hydroxylamine: Regioselective, Facile and Straightforward Entry to 5-Substituted 3-Aminoisoxazoles European Journal of Organic Chemistry, 2013 (19). pp. 4026-4031. ISSN 1434-193X

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Official URL: http://doi.org/10.1002/ejoc.201300038

Related URL: http://dx.doi.org/10.1002/ejoc.201300038

Abstract

A highly regioselective synthesis of 5-substituted 3-aminoisoxazoles has been achieved by a one-pot three-component coupling of β-oxo dithioesters, amines and hydroxylamine in ethanol at reflux via an in situ generated β-oxo thioamide intermediate. The mechanism of the reaction has been established experimentally and shown to be in agreement with the HSAB theory

Item Type:Article
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