Fe/S-Catalyzed Redox Condensation of o-Nitrophenols with Isothiocyanates to 2-Aminobenzoxazoles

Org Lett. 2023 Jul 14;25(27):5145-5150. doi: 10.1021/acs.orglett.3c01897. Epub 2023 Jul 2.

Abstract

As frequently encountered byproducts of isocyanate chemistry, hydrogen sulfide and related sulfur containing compounds should be treated in a safe way to lower their adverse health and environmental effects, especially in large scale syntheses. As a proof of concept, we report herein an example of in situ recycling of sulfur byproduct to reductant in the synthesis of bioactive 2-aminobenzoxazoles 3. Using an Fe/S catalytic system, this heterocyclic scaffold could be obtained from o-nitrophenols 1 with isothiocyates 2 via direct redox condensation consisting of reduction of the nitro group of 1 by the sulfur moiety of 2.

MeSH terms

  • Catalysis
  • Isothiocyanates*
  • Nitrophenols*
  • Oxidation-Reduction
  • Sulfur
  • Sulfur Compounds

Substances

  • Isothiocyanates
  • Nitrophenols
  • Sulfur
  • Sulfur Compounds