Journal
TETRAHEDRON LETTERS
Volume 55, Issue 5, Pages 979-981Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.12.016
Keywords
1,2,4-Oxadiazole; O-Acylamidoxime; Tetrabutylammonium hydroxide; Tetrabutylammonium fluoride
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Tetrabutylammonium hydroxide (TBAH) is an efficient and mild alternative to tetrabutylammonium fluoride (TBAF) for base catalyzed cyclizations of 1,2,4-oxadiazoles from O-acylamidoximes. For most 3,5-substituted 1,2,4-oxadiazoles the reactions were dramatically accelerated by addition of 0.1 equiv of TBAH at room temperature. This method was also more generally applicable allowing for a wider range of substrates. Additionally, due to the absence of fluoride, TBAH will not result in corrosion of reactor vessels and therefore is better suited for large-scale synthesis. (C) 2014 Published by Elsevier Ltd.
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