Transition-metal-catalyzed selective cyclization strategy to 2-substituted benzofurans and indoles en route to the oxa analogues of isocryptolepine

Satrajit Indu, Parthasarathi Subramanian, Krishna P. Kaliappan

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A selective catalytic route to benzofurans and indoles from similar starting materials has been developed. A two-step protocol that involves a transition-metal-catalyzed domino Sonogashira coupling between 2-ethynylanilines and 2-iodophenols followed by selective O- and N-cyclizations afforded 2-(benzofuran-2-yl)anilines and 2-(indol-2-yl)phenols, respectively. The 2-(benzofuran-2-yl)anilines were further utilized in a Lewis acid catalyzed Pictet-Spengler-type cyclization to prepare the oxa analogues of isocryptolepine.

Original languageEnglish
Pages (from-to)7193-7202
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number32
DOIs
Publication statusPublished - 2014 Nov
Externally publishedYes

Keywords

  • Cross-coupling
  • Cyclization
  • Domino reactions
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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