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Issue 27, 2016
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Synthesis of 3,4,5-trisubstituted isoxazoles via 1,3-dipolar cycloaddition/SO2 extrusion of benzoisothiazole-2,2-dioxide-3-ylidenes with nitrile oxides

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Abstract

A straightforward synthesis of 3,4,5-trisubstituted isoxazole derivatives via 1,3-dipolar cycloaddtion/SO2 extrusion of benzoisothiazole-2,2-dioxide-3-ylidenes with nitrile oxides is reported using 4 Å molecular sieves as a dehydrochlorinating agent. This tandem ring closing/ring opening synthesis of 3,4,5-trisubstituted isoxazoles is the first of its kind. This methodology would enrich the synthetic chemistry of isoxazoles from easily available starting materials and benefit the discovery of novel isoxazoles with potential biological activities.

Graphical abstract: Synthesis of 3,4,5-trisubstituted isoxazoles via 1,3-dipolar cycloaddition/SO2 extrusion of benzoisothiazole-2,2-dioxide-3-ylidenes with nitrile oxides

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Article information


Submitted
14 Dec 2015
Accepted
19 Feb 2016
First published
22 Feb 2016

RSC Adv., 2016,6, 22519-22525
Article type
Paper

Synthesis of 3,4,5-trisubstituted isoxazoles via 1,3-dipolar cycloaddition/SO2 extrusion of benzoisothiazole-2,2-dioxide-3-ylidenes with nitrile oxides

G. Cao, Y. Wang, T. Cui, L. Huang and D. Teng, RSC Adv., 2016, 6, 22519
DOI: 10.1039/C5RA26718H

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