Solid-phase syntheses of 6-arylpyridazin-3(2H)-ones.
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.
Salives
Richard
R
IRCOF, Laboratoire de Chimie Organique Fine et Hétérocyclique, UPRES-A 6014, INSA, B.P. 08, 76131 Mont St Aignan Cedex, France.
Dupas
Georges
G
Plé
Nelly
N
Quéguiner
Guy
G
Turck
Alain
A
George
Pascal
P
Sevrin
Mireille
M
Frost
Jonathan
J
Almario
Antonio
A
Li
Adrien
A
D001897:Boronic Acids / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D020650:Combinatorial Chemistry Techniques; D003432:Cross-Linking Reagents; D006835:Hydrazones / Q000138:chemical synthesis*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D008956:Models, Chemical; D011724:Pyridazines / Q000138:chemical synthesis*; D012117:Resins, Synthetic / Q000737:chemistry
D001897:Boronic Acids; D003432:Cross-Linking Reagents; D006835:Hydrazones; D006841:Hydrocarbons, Aromatic; D011724:Pyridazines; D012117:Resins, Synthetic