Issue 0, 1984
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Regioselective Claisen rearrangements in indoles

Christopher J. Moody  

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.

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Article information

DOI
https://doi.org/10.1039/P19840001333
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 1333-1337

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Regioselective Claisen rearrangements in indoles

C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1984, 1333 DOI: 10.1039/P19840001333

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