The Hofmann-like fragmentation induced by n-acylation of 1-methyl-1-AZA-4-cyclanones and its use in the synthesis of 2-AZA-hydrindanones and 2-AZA-decalones
1988; Elsevier BV; Volume: 29; Issue: 27 Linguagem: Inglês
10.1016/0040-4039(88)85147-5
ISSN1873-3581
AutoresJean Lévy, Jean‐Yves Laronze, Janos-Sapi,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe N-methyl-piperidone 4a was fragmented to the vinylketonic acrylamide 9a by successive treatment with acryloyl chloride and Hunig's base. The 2-azahydrindandione 13a resulted from the cyclization of 9a in the form of its enol dimethylterbutyl ether. N-methyl-azepinone 4b was transformed in a similar way to the two epimeric 2-azadecalindiones 13b + 14b in four steps only.
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