The dicarbonylation of indoles via Friedel–Crafts reaction with dicarbonyl nitrile generated in situ and retro-cyanohydrination

The dicarbonylation of indoles via Friedel–Crafts reaction with dicarbonyl nitrile generated in situ and retro-cyanohydrination

A novel one-pot tandem reaction of indole and β-carbonyl nitrile to generate dicarbonyl indoles has been developed. This tandem process involves α-oxonation of the β-carbonyl nitrile to afford α,β-dicarbonyl nitrile, Friedel–Crafts reaction with indoles and subsequent retro-cyanohydrination of cyano...

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Veröffentlicht in:RSC advances 2016-01, Vol.6 (50), p.44029-44033
Hauptverfasser: Yan, Jianwei, He, Guangjie, Yan, Fulin, Zhang, Jixia, Zhang, Guisheng
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols
Cascade chemical reactions
Friedel-Crafts reaction
Indoles
Nitriles
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Beschreibung
Zusammenfassung:A novel one-pot tandem reaction of indole and β-carbonyl nitrile to generate dicarbonyl indoles has been developed. This tandem process involves α-oxonation of the β-carbonyl nitrile to afford α,β-dicarbonyl nitrile, Friedel–Crafts reaction with indoles and subsequent retro-cyanohydrination of cyano tertiary alcohol form dicarbonyl indoles.
ISSN:2046-2069
2046-2069
DOI:10.1039/C6RA04016K