Journal
TETRAHEDRON
Volume 69, Issue 35, Pages 7471-7480Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.06.032
Keywords
Cycloisomerization; N-Iodosuccinimide; 1H-Indole-2-carbaldehydes; Propargylic alcohols; Water
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Funding
- College of Science Start-Up Grant from Nanyang Technological University
- Science and Engineering Research Council Grant from A*STAR, Singapore [092 101 0053]
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A N-iodosuccinimide (NIS)-mediated method to prepare 1H-indole-2-carbaldehydes efficiently from cycloisomerization of 1-(2-aminophenyl)prop-2-yn-1-ols is described. The reaction is operationally straightforward and accomplished in good to excellent yields (48-91%) from a wide range of alcohol substrates that are low cost, easily accessible, and ecologically benign. The utility of the approach as a potential scale-up strategy for the synthesis of the indole was exemplified by the large-scale synthesis of one example in an excellent yield. The synthetic utility of this chemistry was also demonstrated in a formal synthesis of (R)-calindol. (C) 2013 Elsevier Ltd. All rights reserved.
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