A mild method for the formation and in situ reaction of imidoyl chlorides: conversion of pyridine-1-oxides to 2-aminopyridine amides

Org Lett. 2002 Sep 5;4(18):3127-9. doi: 10.1021/ol0264556.

Abstract

[reaction: see text] A mild, practical, one-pot method for the generation of imidoyl chlorides and their subsequent in situ reaction with pyridine-1-oxides is described. The imidoyl chlorides were formed from the reaction of secondary amides with a stoichiometric amount of oxalyl chloride and 2,6-lutidine in CH(2)Cl(2) at 0 degrees C. Upon warming of the reaction mixture to room temperature in the presence of pyridine-1-oxides, a rapid conversion to 2-aminopyridine amides was observed in moderate to excellent isolated yields.

MeSH terms

  • Amides / chemical synthesis*
  • Aminopyridines / chemical synthesis*
  • Chemistry, Pharmaceutical / methods
  • Chlorides / chemistry
  • Oxalates / chemistry
  • Oxides / chemistry

Substances

  • Amides
  • Aminopyridines
  • Chlorides
  • Oxalates
  • Oxides
  • oxalyl chloride
  • alpha-aminopyridine