Ring expansion of sulfur substituted p-quinamines: regiospecific synthesis of 4-aminotropones

Chem Commun (Camb). 2005 Feb 28:(8):1007-9. doi: 10.1039/b414666b. Epub 2005 Jan 5.

Abstract

Synthesis of 4-aminotropones through a cyclization-ring expansion process occurs in a single step and with excellent yields from 4-amino-2,5-cyclohexadienones (p-quinamines) bearing a 4-sulfinyl or sulfonyl methyl group.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Cyclization
  • Molecular Structure
  • Stereoisomerism
  • Sulfur / chemistry*
  • Tropolone / analogs & derivatives*
  • Tropolone / chemical synthesis
  • Tropolone / chemistry

Substances

  • Alkaloids
  • quinamine
  • Sulfur
  • Tropolone
  • tropone