Synthesis of 3-carboxylated indoles through a tandem process involving cyclization of 2-ethynylanilines followed by CO2 fixation in the absence of transition metal catalysts

Kiyofumi Inamoto, Narumi Asano, Yuka Nakamura, Misato Yonemoto, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)

Abstract

In this study, a facile synthesis of 3-carboxylated indoles involving a tandem-type cyclization of 2-ethynylanilines and subsequent CO2 fixation at the 3-position of the indole ring is realized. The reaction proceeds efficiently at 65 °C under 10 atm of CO2, giving rise to variously substituted 3-carboxylated indoles, generally in high yields. An inorganic base, such as K2CO3, is the only reagent required, and the addition of transition metal catalysts is not necessary. The method provides a novel, simple, and promising strategy for CO2 fixation in the research field of heterocyclic chemistry.

Original languageEnglish
Pages (from-to)2622-2625
Number of pages4
JournalOrganic letters
Volume14
Issue number10
DOIs
Publication statusPublished - 2012 May 18

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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