Synthesis of benzo[

A] carbazoles via cyanide-catalyzed imino-Stetter reaction/Friedel-Crafts reaction sequence

Jiye Jeon, Cheol-Hong Cheon

Research output: Contribution to journalArticle

Abstract

A new protocol to access benzo[a]carbazole derivatives was developed, via the cyanide-catalyzed imino-Stetter reaction/Friedel-Crafts reaction sequence. The cyanide-catalyzed imino-Stetter reaction of aldimines derived from 2-aminochalcones and aromatic aldehydes provided the corresponding 2-aryl-3-arenacylindole derivatives, which could be converted to benzo[a]carbazoles via intramolecular Friedel-Crafts ractions. Various 2-aminochalcones and aldehydes were applicable to this protocol, affording the desired benzo[a]carbazoles in good to high yields. Furthermore, we also developed a sequential protocol for the construction of benzo[a]carbazoles from 2-aminochalcones and aldehydes, without isolating any intermediates.

Original languageEnglish
Pages (from-to)456-467
Number of pages12
JournalOrganic Chemistry Frontiers
Volume6
Issue number4
DOIs
Publication statusPublished - 2019 Feb 21

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Carbazoles
Friedel-Crafts reaction
Cyanides
Aldehydes
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

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Synthesis of benzo[ : A] carbazoles via cyanide-catalyzed imino-Stetter reaction/Friedel-Crafts reaction sequence. / Jeon, Jiye; Cheon, Cheol-Hong.

In: Organic Chemistry Frontiers, Vol. 6, No. 4, 21.02.2019, p. 456-467.

Research output: Contribution to journalArticle

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