A new approach to the synthesis of 4-(N-aryl)carbamoylmethyl-4,5-dihydropyridazin-3(2H)-ones

✍ Scribed by Alexander V. Stepakov; Michail A. Kinzhalov; Vitaly M. Boitsov; Liubov V. Stepakova; Galina L. Starova; Sergey Yu. Vyazmin; Elena V. Grinenko

• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 676 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2011.04.038

✦ Synopsis

Reaction of N-aryl substituted maleimides with aliphatic ketazines leads to the formation of 4,5-dihydropyridazin-3(2H)-ones in moderate yields. The reaction proceeds through 1,4-addition of an azine to the maleimide double bond, as confirmed by separation of the corresponding adducts in some cases, which are then converted into 4,5-dihydropyridazin-3(2H)-ones. In addition, the solid-state synthesis of 4,5-dihydropyridazin-3(2H)-ones is demonstrated for the first time.