Synthesis of Some New N-[1-(Benzocoumarin-3`-yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives
American Journal of Heterocyclic Chemistry
Volume 2, Issue 1, December 2016, Pages: 32-38
Received: Dec. 10, 2016; Accepted: Dec. 22, 2016; Published: Jan. 12, 2017
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Authors
Hussein A. Emam, Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Saber M. Hassan, Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Ahmed M. El-Agrody, Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Ahmed H. Bedair, Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Mahmoud M. Abdelall, Chemistry Department, Faculty of Science and Arts, Al-Baha University, Al-Baha, Saudi Arabia
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Abstract
Condensation of 3-acetylbenzo[5,6]coumarin (1) with hydrazine-carbodithioate esters and/or thiocarbohydrazide gave the corresponding N-[1-(benzocoumarin-3`-yl)ethylidene]hydrazonecarbodithioate (2a,b) and 1,5-bis[1-(benzocoumarin-3`-yl)ethylidene]thiocarbohydrazide (3) respectively. Treatment of 2a with ethanolic ammonia solution and/or amines gave the corresponding thiosemicarbazone derivatives (4a-f). The reactions of 4a-f with ethyl bromoacetate/AcONa and ω-bromo derivatives were investigated, where thiazolidinones 5, 6 and thiazoles (9a,b) were obtained. Moreover, hydrazonecarbodithioate (2) underwent heterocycliczation upon treatment with hydrazonoyl halides (10) with Et3N to give the corresponding 2,3-dihydro-1,3,4-thiadiazoles (11a-d) via 1,3-dipolar cycloaddition and/or nuclophilic substiution. The structures of the new derivatives were elucidated by elemental analysis, IR, PMR and mass spectra.
Keywords
Benzocoumarin, 1,3,4-Thiadiazol, Thiazolidinone
To cite this article
Hussein A. Emam, Saber M. Hassan, Ahmed M. El-Agrody, Ahmed H. Bedair, Mahmoud M. Abdelall, Synthesis of Some New N-[1-(Benzocoumarin-3`-yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives, American Journal of Heterocyclic Chemistry. Vol. 2, No. 1, 2016, pp. 32-38. doi: 10.11648/j.ajhc.20160201.16
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Copyright © 2016 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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