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The role of a Lewis acid in the Nenitzescu indole synthesis

✍ Scribed by Valeriya S. Velezheva; Andrey I. Sokolov; Albert G. Kornienko; Konstantin A. Lyssenko; Yulia V. Nelyubina; Ivan A. Godovikov; Alexander S. Peregudov; Andrey F. Mironov

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
348 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

A highly efficient Lewis acid-catalyzed method for the Nenitzescu synthesis of 5-hydroxyindoles with a range of substituents at N-1 and C-3 and symmetric 5,5 0 -dihydroxydiindoles has been developed. The amount of the catalyst (10-100 mol %) required depended on the nature of the enaminone component. It has been shown that Lewis acid plays a role in enaminone component activation through an enamine-ZnC1 2 complex followed by its deprotonation.

πŸ“œ SIMILAR VOLUMES

Lewis acid catalyzed nenitzescu indole s
Lewis acid catalyzed nenitzescu indole synthesis
✍ Valeriya S. Velezheva; Albert G. Kornienko; Sergey V. Topilin; Ascar D. Turashev πŸ“‚ Article πŸ“… 2006 πŸ› Journal of Heterocyclic Chemistry 🌐 English βš– 131 KB

## Abstract magnified image 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, e

Lewis acid catalyzed rapid synthesis of
Lewis acid catalyzed rapid synthesis of 5-hydroxy-benzo[g]indole scaffolds by a modified Nenitzescu reaction
✍ Moyurima Borthakur; Shyamalee Gogoi; Junali Gogoi; Romesh C. Boruah πŸ“‚ Article πŸ“… 2010 πŸ› Elsevier Science 🌐 French βš– 595 KB

A fast solvent-less synthesis of 5-hydroxy-benzo[g]indole scaffolds is accomplished from Lewis acid-catalyzed one-pot reaction of naphthoquinone, x-morpholinoacetophenone, and urea under microwave irradiation. The key step in the synthesis is the Michael addition followed by in situ aza cyclization