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

Org Lett. 2012 May 18;14(10):2622-5. doi: 10.1021/ol300958c. Epub 2012 May 7.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Carbon Dioxide / chemistry*
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure

Substances

  • Aniline Compounds
  • Carboxylic Acids
  • Indoles
  • Carbon Dioxide