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Molecules 2011, 16(6), 4549-4559; doi:10.3390/molecules16064549

Microwave Assisted Synthesis and Unusual Coupling of Some Novel Pyrido[3,2-f][1,4]thiazepines

Department of Chemistry, Faculty of Science, Cairo University, Egypt
Department of Chemistry, Faculty of Science, Fayoum University, Egypt
Current address: Department of Chemistry, Faculty of Science, Taif University, Saudi Arabia.
Author to whom correspondence should be addressed.
Received: 23 March 2011 / Revised: 7 May 2011 / Accepted: 25 May 2011 / Published: 31 May 2011
(This article belongs to the Special Issue Microwave Assisted Synthesis)
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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.
Keywords: microwave; monothiomalonamide; pyridinecarboxamide; pyridothiazepines; coupling microwave; monothiomalonamide; pyridinecarboxamide; pyridothiazepines; coupling
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Faty, R.M.; Youssef, M.M.; Youssef, A.M. Microwave Assisted Synthesis and Unusual Coupling of Some Novel Pyrido[3,2-f][1,4]thiazepines. Molecules 2011, 16, 4549-4559.

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