Four-component reactions toward fused heterocyclic rings

Org Lett. 2009 Nov 19;11(22):5314-7. doi: 10.1021/ol902279m.

Abstract

A multicomponent reaction between H(2), CO, an unsaturated carboxylic acid derivative, and binucleophiles has been discovered. This process represents a combination of diversity-oriented synthesis and multicomponent reactions including amidation and hydroformylation, followed by nucleophilic addition to an N-acyliminium ion allowing the generation of six new bonds. Using pi-nucleophiles, the sequence turns into a multicomponent Pictet-Spengler reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Monoxide / chemistry*
  • Carboxylic Acids / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Hydrogen / chemistry*
  • Imines / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Carboxylic Acids
  • Heterocyclic Compounds
  • Imines
  • Carbon Monoxide
  • Hydrogen