Regioselective synthesis of nitrosoimidazoheterocycles using tert-butyl nitrite

Org Biomol Chem. 2015 Aug 28;13(32):8717-22. doi: 10.1039/c5ob01345c. Epub 2015 Jul 16.

Abstract

A simple and practical method has been developed for the regioselective nitrosylation of imidazopyridines via C(sp(2))-H bond functionalization using tert-butyl nitrite under mild reaction conditions in a short time. A library of 3-nitrosoimidazopyridines with broad functionalities was synthesized in near quantitative yields. The present protocol is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Molecular Structure
  • Nitrites / chemistry*
  • Nitroso Compounds / chemical synthesis*
  • Nitroso Compounds / chemistry
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Stereoisomerism
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry

Substances

  • Imidazoles
  • Nitrites
  • Nitroso Compounds
  • Pyridines
  • Thiazoles
  • n-butyl nitrite