Regioselective Claisen rearrangements in indoles
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1333-1337
- https://doi.org/10.1039/p19840001333
Abstract
The Claisen rearrangement of several ethyl allyloxyindole-2-carboxylates is described. These indoles are readily prepared by the thermolysis of azidocinnamates in toluene, which undergo concomitant ring closure and Claisen rearrangement when heated in bromobenzene. Rearrangement of the 6-allyloxy derivatives (10) and (17) proceeds regioselectively to give the corresponding 7-allyl-6-hydroxyindoles. The method has been used to prepare 7-(1,1-dimethylallyl)-, 7-(3-methylbut-2-enyl)-, and 7-linalyl-indoles in synthetically useful reactions.Keywords
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