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Trends in Heterocyclic Chemistry   Volumes    Volume 5 
Abstract
Synthesis and reactivity of 1H-indol-3(2H)-one and related compounds
J.-Y. Mérour, S. Piroëlle, B. Joseph
Pages: 115 - 126
Number of pages: 12
Trends in Heterocyclic Chemistry
Volume 5 

Copyright © 1997 Research Trends. All rights reserved

ABSTRACT
 
Among the diverse reactions leading to indol-3(2H)-ones 1-3, oxidation methods such as Baeyer-Villiger rearrangement of 3-formylindoles or ozonolysis of 3-methyleneindolines are promising. The reactivity of 1 is illustrated by the synthesis of pharmacologically active compounds such as tryptamines via Horner-Emmons condensation or piperazinoindoles. Aldolisation reactions of 1 give access to α,β ethylenic ketones which synthetic potential is examined (reduction, oxidation, inverse electron demand Diels-Alder). The behavior of related compounds 3-hydroxyindole-2-carboxylic acid alkyl ester is also illustrated with 2 examples and the triflate chemistry (palladium) of this family is throughly evocated.
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