Synthesis of diverse 4,5-dihydro-3(2H)-pyridazinones on Wang resin

J Pharm Pharmacol. 2001 Jul;53(7):981-5. doi: 10.1211/0022357011776225.

Abstract

An efficient solid-phase synthesis of structurally diverse 4,5-dihydro-3(2H)-pyridazinones is described using readily available substituted 4-oxo-butanoic acids. Polymer-supported gamma-keto-esters prepared from Wang resin reacted with several hydrazines to afford the corresponding hydrazones. A protocol developed in mild conditions without isolating the intermediate hydrazone led to pyridazinones in good yields after a cyclization cleavage approach. This successful strategy represents an attractive method for a rapid synthesis of heterocyclic libraries for biological evaluation.

MeSH terms

  • Butyrates / chemical synthesis
  • Hydrazines / chemical synthesis
  • Hydrazones / chemical synthesis
  • Pyridazines / chemical synthesis*
  • Resins, Plant / chemical synthesis*

Substances

  • Butyrates
  • Hydrazines
  • Hydrazones
  • Pyridazines
  • Resins, Plant