Author： Gad-Elkareem Mohamed Abdel-Fattah Azza Elneairy Mohamed
Publisher： Taylor & Francis Ltd
ISSN： 1042-6507
Source： Phosphorus, Sulfur, and Silicon and the Related Elements, Vol.181, Iss.4, 2006-04, pp. : 891-911
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Abstract
Nicotinic acid esters 3a–c were prepared by the reaction of pyridine-2(1 H )-thione derivative 1 with a-halo-reagents 2a–c. Compounds 3a–c underwent cyclization to the corresponding thieno[2, 3- b ]pyridines 4a–c via boiling in ethanol/piperidine solution. Compounds 4a–c condensed with dimethylformamide-dimethylacetal (DMF-DMA) to afford 3-{[( N , N -dimethylamino)methylene]amino}thieno[2, 3- b ]- pyridine derivatives 6a–c. Moreover, compounds 4a–c and 6a–c reacted with different reagents and afforded the pyrido[3',2': 4 , 5 ]thieno[3, 2- d ]pyrimidine derivatives 10a–d, 11a–c, 12a,b, 14a,b, 17, and 19. In addition, pyrazolo[3, 4- b ]pyridine derivative 20 (formed via the reaction of 1 with hydrazine hydrate) reacted with ethylisothiocyanate yielded the thiourea derivative 21. Compound 21 reacted with a-halocarbonyl compounds to give the 3-[(3 H -thiazol-2-ylidene)amino]-1 H -pyrazolo[3, 4- b ]pyridine derivatives 23a–c, 25, and 27a,b.
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