Lewis acid mediated one-pot synthesis of aryl/heteroaryl-fused carbazoles involving a cascade Friedel-Crafts alkylation/electrocyclization/aromatization reaction sequence

Radhakrishnan Sureshbabu, Velu Saravanan, Vasudevan Dhayalan, Arasambattu K. Mohanakrishnan

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

A Lewis-acid-mediated domino reaction of 2/3-(bromomethyl)indoles with arenes/heteroarenes led to the formation of the corresponding annulated carbazoles. This three-step one-pot transformation proceeds by sequential Lewis acid catalysed Friedel-Crafts alkylation, electrocyclization and aromatization reactions. The strategy is highly efficient for the assembly of complex aryl/heteroaryl-fused carbazoles.

Original languageEnglish
Pages (from-to)922-935
Number of pages14
JournalEuropean Journal of Organic Chemistry
Issue number5
DOIs
StatePublished - 1 Feb 2011
Externally publishedYes

Keywords

  • Annulation
  • Domino reactions
  • Electrocyclization
  • Friedel-Crafts reactions
  • Fused ring systems

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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