Solid-phase syntheses of 6-arylpyridazin-3(2H)-ones

J Comb Chem. 2005 May-Jun;7(3):414-20. doi: 10.1021/cc049845n.

Abstract

The 3-chloropyridazine moiety was immobilized on a Wang resin, using two different methodologies. The first of these involved direct nucleophilic substitution of 3,6-dichloropyridazine with the alcoholate of Wang resin. The experimental conditions were optimized. The second method involved a Mitsunobu reaction between the Wang resin and 6-chloropyridazin-3-ol during which a problem of regioselectivity was observed. The so-obtained chloropyridazine-containing resins were subsequently reacted with various arylboronic acids under Suzuki conditions. Acid cleavage yielded 6-arylpyridazin-3(2H)-ones with high chemical purity.

MeSH terms

  • Boronic Acids / chemistry
  • Chemistry, Pharmaceutical*
  • Combinatorial Chemistry Techniques*
  • Cross-Linking Reagents
  • Hydrazones / chemical synthesis*
  • Hydrocarbons, Aromatic / chemistry*
  • Models, Chemical
  • Pyridazines / chemical synthesis*
  • Resins, Synthetic / chemistry

Substances

  • Boronic Acids
  • Cross-Linking Reagents
  • Hydrazones
  • Hydrocarbons, Aromatic
  • Pyridazines
  • Resins, Synthetic