Iodine-catalyzed regioselective thiolation of imidazo[1,2-a]pyridines using sulfonyl hydrazides as a thiol surrogate

Org Biomol Chem. 2015 Mar 21;13(11):3314-20. doi: 10.1039/c5ob00033e.

Abstract

Iodine-catalyzed regioselective sulfenylation of imidazo[1,2-a]pyridines via C(sp(2))-H bond functionalization has been achieved using sulfonyl hydrazides as a thiol surrogate. A library of 3-sulfanylimidazopyridines with broad functionalities was synthesized under metal and oxidant-free practical reaction conditions. This methodology is also applicable for the regioselective sulfenylation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrazines / chemistry*
  • Iodine / chemistry*
  • Molecular Structure
  • Pyridines / chemistry*
  • Stereoisomerism
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Hydrazines
  • Pyridines
  • Sulfhydryl Compounds
  • Iodine
  • imidazo(1,2-a)pyridine