A convenient one-pot preparation of 2-methyl-3-(phenylthio- methyl)quinolines from Morita-Baylis-Hillman adducts and their oxidation to the corresponding sulfones

Molecules. 2012 May 3;17(5):5081-94. doi: 10.3390/molecules17055081.

Abstract

A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3-(phenylthiomethyl)quinolines were transformed into 2-methyl-3-(phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid / chemistry
  • Cyclization
  • Iron / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Quinolines / chemical synthesis*
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*
  • Sulfones / chemistry*

Substances

  • Quinolines
  • Sulfhydryl Compounds
  • Sulfones
  • Iron
  • Acetic Acid