Lewis acid catalyzed nenitzescu indole synthesis

A novel method for Lewis acid catalyzed Nenitzescu indole syntheses of 5‐hydroxyindoles bearing different substituents in positions 1 )Alk, Bn, Ar), 2 )Me, Et, Ph), and 3 )COOEt, COMe, CONHPh) as well as tricyclic derivatives are reported. The method is simple, rapid, efficient, and allows preparati...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2006-07, Vol.43 (4), p.873-879
Main Authors: Velezheva, Valeriya S., Kornienko, Albert G., Topilin, Sergey V., Turashev, Ascar D., Peregudov, Alexander S., Brennan, Patrick J.
Format: Article
Language:English
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Summary:A novel method for Lewis acid catalyzed Nenitzescu indole syntheses of 5‐hydroxyindoles bearing different substituents in positions 1 )Alk, Bn, Ar), 2 )Me, Et, Ph), and 3 )COOEt, COMe, CONHPh) as well as tricyclic derivatives are reported. The method is simple, rapid, efficient, and allows preparation of hydroxyindoles from 1,4‐benzoquinone and enamines in good to excellent yields with the use of low‐polar solvents in the presence of weak Lewis acids catalysts. The formation of 5‐hydroxyindoles under such mild conditions is explained in terms of a non‐redox mechanism.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570430410