S. Y. Hassan
2007
Citations
0
Influential Citations
4
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Four series of substituted furan and pyrrole have been synthesized. The first series was prepared by cyclization of the key intermediates ethyl 5-[(4-substituted thiosemicarbazido)methyl]-2-methylfuran-3-carboxylates 2a-2d and 1-[(4-acetyl-5-methyl-1H-pyrrol-2-yl)methylene]-4-substituted thiosemicarbazides 8a-8d with chloroacetic acid or (ethyl bromoacetate) to afford the corresponding 4-oxo-3-substituted thiazolidin-2-ylidene 3a-3d or 3-substituted thiazolidin-4-one 9a-9d. On the other hand, heating of the intermediates 2a-2d or 8a-8d with acetic anhydride afforded the corresponding (N-substituted acetylamino)-2,3-dihydro-[1,3,4]thiadiazol-2-yl derivatives 4a-4d and [1,3,4]thiadiazol-2-yl-N-substituted acetamide 10a-10d respectively, while cyclization with p-bromophenacyl bromide gave rise to the corresponding 3-substituted thiazol-2-yl-ylidene 5a-5d and 11a-11d respectively. Furthermore, 4-oxo-3-substituted thioureido-thiazolidin-2-yl 6a-6d or 4-oxo-thiazolidin-3-yl-3-substituted thiourea 12a-12d were obtained by reaction of the intermediates 2a-2d or 8a-8d with thioglycolic acid. Some of the synthesized compounds showed promising antimicrobial activities.