Facile synthesis of substituted 3-aminofurans through a tandem reaction of N-sulfonyl-1,2,3-triazoles with propargyl alcohols

Org Biomol Chem. 2016 Apr 28;14(16):3878-82. doi: 10.1039/c6ob00377j. Epub 2016 Mar 8.

Abstract

A relay catalysis strategy for substituted 3-aminofurans synthesis has been developed. This transformation involves a tandem reaction sequence through aza-vinyl-rhodium(ii) carbene O-H bond insertion, thermal propargyl-Claisen rearrangement and gold(i)-catalyzed intramolecular cyclization. More importantly, the current strategy employs simple feedstocks as starting materials, providing substituted 3-aminofurans in a highly efficient manner.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Propanols / chemistry*
  • Triazoles / chemistry*

Substances

  • Alkynes
  • Furans
  • Propanols
  • Triazoles
  • propargyl alcohol