Microwave Assisted Synthesis and Unusual Coupling of Some Novel Pyrido[3,2-f][1,4]thiazepines
| العنوان: | Microwave Assisted Synthesis and Unusual Coupling of Some Novel Pyrido[3,2-f][1,4]thiazepines |
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| المؤلفون: | Rasha A. M. Faty, Mohamed M. Youssef, Ayman Youssef |
| المصدر: | Molecules; Volume 16; Issue 6; Pages: 4549-4559 BASE-Bielefeld Academic Search Engine Molecules, Vol 16, Iss 6, Pp 4549-4559 (2011) Molecules |
| بيانات النشر: | Molecular Diversity Preservation International, 2011. |
| سنة النشر: | 2011 |
| مصطلحات موضوعية: | microwave, Thiazepines, pyridothiazepines, Organic Chemistry, monothiomalonamide, pyridinecarboxamide, coupling, Pharmaceutical Science, Medicinal chemistry, Microwave assisted, Article, Analytical Chemistry, lcsh:QD241-441, chemistry.chemical_compound, lcsh:Organic chemistry, chemistry, Chemistry (miscellaneous), Ethyl acetoacetate, Drug Discovery, Molecular Medicine, Organic chemistry, Physical and Theoretical Chemistry, Microwaves, Microwave |
| الوصف: | 3-Amino-3-thioxopropanamide (1) reacted with ethyl acetoacetate to form 6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide (2), which reacted with α-haloketones 3 to produce 2,3-disubstituted-8-hydroxy-6-methyl-2H,5H-pyrido[3,2-f]-[1,4]thiazepin-5-ones 4a-c. Benzoylation of 4c led to the formation of the dibenzoate derivative 9. Compounds 4a-c could be prepared stepwise through the formation of S-alkylated derivatives 10a-c. Compounds 2, 4a-c, 9 and 10a-c were prepared using microwave as a source of heat, and gave better yields in shorter times than those achieved by traditional methods. Coupling of 4a-c with arenediazonium chlorides proceeded unusually to give the 6-hydroxy-4-methyl-2-(arylazo)thieno[2,3-b]pyridin-3(2H)-one ring contraction products 14. Structures of the newly synthesized compounds were proven by spectral and chemical methods. |
| وصف الملف: | application/pdf |
| اللغة: | English |
| تدمد: | 1420-3049 |
| DOI: | 10.3390/molecules16064549 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2136b1eae5d2e40fecd5c4233131a789 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....2136b1eae5d2e40fecd5c4233131a789 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 14203049 |
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| DOI: | 10.3390/molecules16064549 |