Synthesis and characterization of thiochromone S,S-dioxides as new photolabile protecting groups

Chem Commun (Camb). 2008 May 14:(18):2103-5. doi: 10.1039/b801860j. Epub 2008 Mar 27.

Abstract

3-Arylthiochromone derivatives were synthesized as new photolabile protecting groups, in which the photoreactivity was switchable based on oxidation of the sulfur atom (sulfide and sulfone); the protected substrates , released the corresponding alcohols, amines or carbonxylic acids almost quantitatively under UV-light in neutral condition and the photoproduct showed high fluorescence intensity.

MeSH terms

  • Alcohols / chemical synthesis
  • Alcohols / chemistry
  • Alcohols / radiation effects
  • Amines / chemical synthesis
  • Amines / chemistry
  • Amines / radiation effects
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / radiation effects
  • Chromones / chemical synthesis*
  • Chromones / chemistry*
  • Chromones / radiation effects
  • Cyclization
  • Molecular Structure
  • Oxides / chemical synthesis*
  • Oxides / chemistry*
  • Oxides / radiation effects
  • Photochemistry
  • Stereoisomerism
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry*
  • Sulfhydryl Compounds / radiation effects
  • Ultraviolet Rays

Substances

  • Alcohols
  • Amines
  • Carboxylic Acids
  • Chromones
  • Oxides
  • Sulfhydryl Compounds