Nucleophilic substitution of azide acting as a pseudo leaving group: one-step synthesis of various aza heterocycles

J Org Chem. 2013 Nov 15;78(22):11335-41. doi: 10.1021/jo401738f. Epub 2013 Oct 24.

Abstract

The reaction of 3-azidopropanoic acid with the carbodiimide-based coupling reagent DIC leads to a six-membered-ring intermediate acting as a versatile precursor to a diverse set of aza heterocycles, including mono-, bi-, and tricyclic compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Azides / chemistry*
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Molecular Structure

Substances

  • Aza Compounds
  • Azides
  • Heterocyclic Compounds