1,3-Dipolar Cycloaddition in the Preparation of New Fused Heterocyclic Compounds via Thermal Initiation

Molecules. 2016 Feb 4;21(2):187. doi: 10.3390/molecules21020187.

Abstract

This paper describes the synthesis of precursors with a benzo[b]furan skeleton for the intramolecular 1,3-dipolar cycloaddition of azomethine ylides prepared from N-substituted 3-allyl-aminobenzo[b]furan-2-aldehydes and secondary amines derived from α-amino acid esters. Reactions were initiated by heating. The products consisted of four fused rings with three stereogenic centers. Their structure and stereochemistry were determined by NMR spectra and X-ray measurements.

Keywords: 1,3-dipolar cycloaddition; 3-amino-benzo[b]furan-2-carbaldehyde; fused heterocycles; thermal initiation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis
  • Azo Compounds / chemistry
  • Cycloaddition Reaction
  • Furans / chemical synthesis*
  • Hot Temperature
  • Molecular Conformation
  • Thiosemicarbazones / chemistry

Substances

  • Aldehydes
  • Azo Compounds
  • Furans
  • Thiosemicarbazones
  • azomethine