1,2,3,4-TETRAHYDRO-1,6-NAPHTHYRIDINES .2. FORMATION AND UNEXPECTED REACTIONS OF 1,2,3,4-TETRAHYDRO-7H-PYRANO[4,3-B]PYRIDINE-2,7-DIONES

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...

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Published inHeterocycles Vol. 36; no. 1; pp. 1 - 6
Main Authors VICTORY, PJ, TEIXIDO, J, BORRELL, JI, BUSQUETS, N
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary: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.
ISSN:0385-5414