Pseudo-five-component reaction between 3-formylchromones, meldrum's acid, isocyanides and primary arylamines: diversity-oriented synthesis of novel chromone-containing peptidomimetics

ACS Comb Sci. 2011 Nov 14;13(6):659-66. doi: 10.1021/co200125a. Epub 2011 Sep 28.

Abstract

An efficient and practical method has been developed for the diversity-oriented synthesis of chromone-containing tripeptides via pseudo-five-component reaction between 3-formylchromones, Meldrum's acid, isocyanides and primary aromatic amines for the generation of a wide range of structurally interesting and pharmacologically significant compounds at ambient temperature. It is worth mentioning that in the course of this reaction, five new bonds (two C-C bonds, two C-N bonds and one C═O bond) are formed. In the present reaction three amide bonds are newly formed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amines / chemistry*
  • Carbon / chemistry
  • Chromones / chemistry*
  • Cyanides / chemistry*
  • Dioxanes / chemistry*
  • Hydrocarbons, Aromatic / chemistry*
  • Models, Chemical
  • Nitrogen / chemistry
  • Oxygen / chemistry
  • Peptidomimetics / chemical synthesis*
  • Peptidomimetics / chemistry
  • Peptidomimetics / pharmacology
  • Temperature

Substances

  • Amides
  • Amines
  • Chromones
  • Cyanides
  • Dioxanes
  • Hydrocarbons, Aromatic
  • Peptidomimetics
  • formylchromone
  • Carbon
  • Meldrum's acid
  • Nitrogen
  • Oxygen