An azomethine ylide approach to complex alkaloid-like heterocycles

J Org Chem. 2007 Apr 13;72(8):3097-9. doi: 10.1021/jo062579a. Epub 2007 Mar 14.

Abstract

The nitrone above is readily available via the intramolecular aza Diels-Alder reaction of an amino acid derived triene in acetic acid. Subsequent treatment of the nitrone in refluxing toluene with substituted actetylenes produced the pictured pyrrole. At lower temperatures a 2,3-dihydroisoxazole, which is the product of a 3+2 dipolar cycloaddition, is produced. Upon heating in refluxing toluene the 2,3-dihydroisoxazole is converted to the pyrrole.

MeSH terms

  • Alkaloids / chemistry*
  • Azo Compounds / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Molecular Structure
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry
  • Thiosemicarbazones / chemistry*

Substances

  • Alkaloids
  • Azo Compounds
  • Heterocyclic Compounds, 4 or More Rings
  • Pyrroles
  • Thiosemicarbazones
  • azomethine