THE HOFFMAN-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

Article abstract of DOI:10.1016/0040-4039(88)85147-5

The N-methyl-piperidone 4a was fragmented to the vinylketonic acrylamide 9a by successive treatment with acryloyl chloride and Huenig'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.