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Communication | Regular issue | Vol 36, No. 1, 1993, pp.1-6
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6138
1,2,3,4-Tetrahydro-1,6-naphthyridines. Part 2. Formation and Unexpected Reactions of 1,2,3,4-Tetrahydro-7H-pyrano[4,3-b]pyridine-2,7-diones

Pedro J. Victory,* Jordi Teixidó, José I. Borrell, and Núria Busquets

*CETS Institut Químic de Sarriá, Universitat Ramon Llull, Departament de Química Organica, Via Augusta 390, E-08017 Barcelona, Spain


The nucleophilic substitution of the enol methoxy group of pyridones (1) by methyl cyanoacetate led to (Z)-5-cyano-6-cyanomethoxycarbonylmethylenepiperidones (6), which underwent cyclization in acid medium to 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2,7-diones (7). Surprisingly, the treatment of 7 with ammonia yielded the 5-cyano-6-cyanomethyl substituted pyridones (11) which were not accessible by reaction of 1 with NaCH2CN.