Journal
TETRAHEDRON
Volume 68, Issue 51, Pages 10456-10463Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.10.007
Keywords
Organocatalysis; Cycloaddition; Azides; 1,2,3-Triazoles; Organoselenium compounds
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Funding
- FAPESP [09/07281-0]
- CNPq [305272/2010-1, 470695/2011-0]
- CAPES
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [09/07281-0] Funding Source: FAPESP
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The beta-enaminone-azide cycloaddition has been used for the synthesis of arylselanyl-1H-1,2,3-triazole-4-carboxylates by reaction of azidophenyl arylselenides with beta-keto-esters. The cycloaddition reactions were performed under mild conditions, reacting various azidophenyl arylselenides and beta-keto-esters using catalytic amount of Et2NH (1 mol %) and the corresponding products were obtained in good to excellent yields. Reactions using focused microwave irradiation reduced considerably the reaction time of this organocatalytic protocol from hours to few minutes, which makes this protocol useful and an attractive approach for the synthesis of high-functionalized 1,2,3-triazoles. (C) 2012 Elsevier Ltd. All rights reserved.
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