Journal
TETRAHEDRON LETTERS
Volume 50, Issue 32, Pages 4677-4682Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.06.004
Keywords
Benzyne; Microwave-assisted reactions; Click reaction; 1H-Benzo[d][1,2,3]triazoles
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The benzotriazoles were prepared by three-component and two-component microwave-assisted [3+2] cycloadditions of various azides to benzyne, 3-methoxybenzyne, and 4,5-difluorobenzyne. In the three-component reaction, the aryne is generated, in the presence of an azide prepared in situ, by the reaction of an o-(trimethylsilylaryl) triflate with either CsF or KF/18-Crown-6. However, in the two-component reactions, a freshly prepared azide is added to the reaction vessel prior to aryne generation. Good to excellent yields of benzotriazoles were obtained in 15-20 min when the microwave-assisted reactions were carried out at 125 degrees C. These reaction times are significantly faster than similar reactions carried out using conventional heating. (C) 2009 Elsevier Ltd. All rights reserved.
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