Formation of benzo[f]-1-indanone frameworks by regulable intramolecular annulations of gem-dialkylthio trienynes

Org Lett. 2015 Feb 20;17(4):782-5. doi: 10.1021/ol5034332. Epub 2015 Feb 5.

Abstract

An atom-economic route to benzo[f]-1-indanone frameworks has been developed starting from the readily available gem-dialkylthio trienynes by intramolecular annulations. The chemoselectivity of the intramolecular cyclizations can be regulated by both the base and the type of gas atmosphere used in the reaction, thus allowing the divergent synthesis of the corresponding functionalized benzo[f]-1-indanones in good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Cyclization
  • Indans / chemical synthesis*
  • Indans / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*

Substances

  • Alkynes
  • Indans
  • Sulfhydryl Compounds
  • benzo(f)-1-indanone