Molecules 2012, 17(6), 6930-6943; doi:10.3390/molecules17066930
Article

Bromination and Diazo-Coupling of Pyridinethiones; Microwave Assisted Synthesis of Isothiazolopyridine, Pyridothiazine and Pyridothiazepines

1 Department of Chemistry, Faculty of Science, Fayoum University, Fayoum 63514, Egypt 2 Department of Chemistry, Faculty of Science, El-Jabal El-Gharby University, Mezda, Gheryan 65096, Libya 3 Department of Chemistry, Faculty of Science, Taif University, Taif 21974, Saudi Arabia Current address: Department of Chemistry, Faculty of Science, Ain-Shams University, Cairo 11566, Egypt. Current address: Department of Chemistry, Faculty of Science, Cairo University, Cairo 12613, Egypt.
* Author to whom correspondence should be addressed.
Received: 25 April 2012; in revised form: 23 May 2012 / Accepted: 31 May 2012 / Published: 6 June 2012
(This article belongs to the Section Organic Synthesis)
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Abstract: Isothiazolopyridines, pyridothiazines and pyridothiazepines are important compounds that possess valuable biological activities. This paper reports on the synthesis of these compounds using both conventional chemical methods and modern microwave techniques. 3-Bromo-6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide, 5-arylazo-6-hydroxy-4-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamides, 3,5-bis-arylazo-6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-caboxamide, 4-methyl-2,3,6,7-tetra-hydroisothiazolo[5,4-b]-pyridine-3,6-dione, 2,2'-(methylene-bis-(sulfanediyl))bis(4-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide), 2-hydroxy-5-methyl-4H-pyrido[3,2-e][1,3]-thiazine-4,7(8H)-dione and 2-arylmethylene-8-hydroxy-6-methyl-2,3,4,5-tetrahydropyrido-[3,2-f][1,4]thiazepine-3,5-diones have been prepared from 6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide. Some of these compounds were prepared using microwave-assisted reaction conditions, that provided higher yields in shorter times than the conventional methods.
Keywords: microwave; bromination; diazo-coupling; pyridinecarboxamide; isothiazolopyridine; pyridothiazine; pyridothiazepine

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MDPI and ACS Style

Youssef, A.M.S.; Azab, M.E.; Youssef, M.M. Bromination and Diazo-Coupling of Pyridinethiones; Microwave Assisted Synthesis of Isothiazolopyridine, Pyridothiazine and Pyridothiazepines. Molecules 2012, 17, 6930-6943.

AMA Style

Youssef AMS, Azab ME, Youssef MM. Bromination and Diazo-Coupling of Pyridinethiones; Microwave Assisted Synthesis of Isothiazolopyridine, Pyridothiazine and Pyridothiazepines. Molecules. 2012; 17(6):6930-6943.

Chicago/Turabian Style

Youssef, Ayman M. S.; Azab, Mohamed E.; Youssef, Mohamed M. 2012. "Bromination and Diazo-Coupling of Pyridinethiones; Microwave Assisted Synthesis of Isothiazolopyridine, Pyridothiazine and Pyridothiazepines." Molecules 17, no. 6: 6930-6943.

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