New synthesis of pyridone derivative from 1-azadiene

✍ Scribed by Mitsuo Komatsu; Shinji Yamamoto; Yoshiki Ohshiro; Toshio Agawa

• Book ID: 104234348
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 230 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82016-5

✦ Synopsis

The reaction of 1-azabutadienes with enolates of substituted acetates gave 3,4-dihydro-2-pyridones which rearrange or dehydrogenate to other isomeric dihydropyridones or pyridones. Thus 1-azabutadienes were found to be good building blocks for pyridone derivatives.

1-Azabutadienes are expected to be useful building blocks for pyridone derivatives whose ring is an important feature of many natural alkaloids and physiologically active subsatnces.

1 Pfleger first reported the formation of a dihydropyridone from N-cinnamilideneaniline and phenylketene, 2 but later the product was proved to be a (2 + 21 cycloadduct, an azetidinone derivative. 3

Afterwards not so many [4 + 21 cycloaddition reactions of 1-azabutadienes including formation of pyridone ring have been reported.

4 These examples of pyridone formation, were, however, rather special ones that have many limitations. 5