Synthesis of diverse 4,5-dihydro-3(2H)-pyridazinones on Wang resin.
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.
Gouault
N
N
UPRES-Synthèse et extraction de molécules à visée thérapeutique-Faculté de Pharmacie 2, Rennes, France.
Cupif
J F
JF
Picard
S
S
Lecat
A
A
David
M
M
D002087:Butyrates / Q000138:chemical synthesis; D006834:Hydrazines / Q000138:chemical synthesis; D006835:Hydrazones / Q000138:chemical synthesis; D011724:Pyridazines / Q000138:chemical synthesis*; D012116:Resins, Plant / Q000138:chemical synthesis*
D002087:Butyrates; D006834:Hydrazines; D006835:Hydrazones; D011724:Pyridazines; D012116:Resins, Plant