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 (1:1 M ratio)...
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| Format: | Article |
| Language: | English |
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Elsevier
2014-11-01
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| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535213003961 |
| _version_ | 1819117620039778304 |
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| author | Yousry A. Ammar Mohamed S.A. El-Gaby Mohamed A. Salem |
| author_facet | Yousry A. Ammar Mohamed S.A. El-Gaby Mohamed A. Salem |
| author_sort | Yousry A. Ammar |
| collection | DOAJ |
| description | 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 (1:1 M ratio) gave pyridine derivatives 11 and 13. Ternary condensation of compound 1, aliphatic aldehydes and malononitrile (1:1:1 M 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. |
| first_indexed | 2024-12-22T05:35:52Z |
| format | Article |
| id | doaj.art-e18c61d664d943299fb82a84e1d54477 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-22T05:35:52Z |
| publishDate | 2014-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-e18c61d664d943299fb82a84e1d544772022-12-21T18:37:19ZengElsevierArabian Journal of Chemistry1878-53522014-11-017561562210.1016/j.arabjc.2013.11.026Cyanoacetanilides intermediates in heterocyclic synthesis. Part 6: Preparation of some hitherto unknown 2-oxopyridine, bipyridine, isoquinoline and chromeno[3,4-c]pyridine containing sulfonamide moietyYousry A. Ammar0Mohamed S.A. El-Gaby1Mohamed A. Salem2Chemistry Department, Faculty of Science, Al-Azhar University Cairo, Nasr City, EgyptChemistry Department, Faculty of Science, Al-Azhar University in Assiut, Assiut, EgyptChemistry Department, Faculty of Science, Al-Azhar University Cairo, Nasr City, EgyptTreatment 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 (1:1 M ratio) gave pyridine derivatives 11 and 13. Ternary condensation of compound 1, aliphatic aldehydes and malononitrile (1:1:1 M 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.http://www.sciencedirect.com/science/article/pii/S1878535213003961Cyanoacetanilide2-PyridoneBipyridineIsoquinoline and chromeno[3,4-c]pyridines |
| spellingShingle | Yousry A. Ammar Mohamed S.A. El-Gaby Mohamed A. Salem 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 Arabian Journal of Chemistry Cyanoacetanilide 2-Pyridone Bipyridine Isoquinoline and chromeno[3,4-c]pyridines |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | Cyanoacetanilide 2-Pyridone Bipyridine Isoquinoline and chromeno[3,4-c]pyridines |
| url | http://www.sciencedirect.com/science/article/pii/S1878535213003961 |
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