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Lewis acid catalyzed nenitzescu indole synthesis

✍ Scribed by Valeriya S. Velezheva; Albert G. Kornienko; Sergey V. Topilin; Ascar D. Turashev; Alexander S. Peregudov; Patrick J. Brennan

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
131 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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.

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› John Wiley and Sons βš– 18 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

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

The role of a Lewis acid in the Nenitzes
The role of a Lewis acid in the Nenitzescu indole synthesis
✍ Valeriya S. Velezheva; Andrey I. Sokolov; Albert G. Kornienko; Konstantin A. Lys πŸ“‚ Article πŸ“… 2008 πŸ› Elsevier Science 🌐 French βš– 348 KB

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

The solid-phase Nenitzescu indole synthe
The solid-phase Nenitzescu indole synthesis
✍ Daniel M Ketcha; Lawrence J Wilson *; David E Portlock πŸ“‚ Article πŸ“… 2000 πŸ› Elsevier Science 🌐 French βš– 157 KB

The solid-phase version of the Nenitzescu indole synthesis of 5-hydroxyindole-3-carboxamides is reported. This process involves initial acetoacetylation of ArgoPore 1 -Rink-NH 2 resin with diketene to aord a polymer-bound acetoacetamide. Formation of the corresponding enaminones via condensation wit