Cyanoacetanilides intermediates in heterocyclic synthesis. Part 6: Preparation of some hitherto unknown 2-oxopyridine, bipyridine, isoquinoline and chromeno[3,4-c]pyridine containing sulfonamide moiety

Treatment of cyanoacetanilide derivative 1 with tetracyanoethylene (2) in dioxane/triethylamine furnished 2-pyridone derivative 6. Aminopyridine 9 was obtained by cyclization of compound 1 with ketene dithioacetal 7/EtONa. Cyclocondensation of 1 with malononitrile and/or acetylacetone (1:1M ratio) g...

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Bibliographic Details
Published in:Arabian journal of chemistry 2014-11, Vol.7 (5), p.615-622
Main Authors: Ammar, Yousry A., El-Gaby, Mohamed S.A., Salem, Mohamed A.
Format: Article
Language:English
Subjects:
2-Pyridone
Bipyridine
Cyanoacetanilide
Isoquinoline and chromeno[3,4-c]pyridines
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Summary:Treatment of cyanoacetanilide derivative 1 with tetracyanoethylene (2) in dioxane/triethylamine furnished 2-pyridone derivative 6. Aminopyridine 9 was obtained by cyclization of compound 1 with ketene dithioacetal 7/EtONa. Cyclocondensation of 1 with malononitrile and/or acetylacetone (1:1M ratio) gave pyridine derivatives 11 and 13. Ternary condensation of compound 1, aliphatic aldehydes and malononitrile (1:1:1M ratio) yielded the 2-pyridones 20a and b. Bipyridines 22a–c were prepared by refluxing of compound 21 with active methylene reagents. Cyclization of chromene derivatives 24 and 28 with malononitrile produced the novel chromeno[3,4-c]pyridine 26 and pyrano[3′,2′:6,7]chromeno[3,4-c]pyridine 29.
ISSN:1878-5352
1878-5379
DOI:10.1016/j.arabjc.2013.11.026