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Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid
Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhaca 20, 31 000 Osijek, Croatia
Department of Chemistry, J. J. Strossmayer University, Franje Kuhaca 20, 31 000 Osijek, Croatia
Department of Biology, J. J. Strossmayer University, Trg Ljudevita Gaja 6, 31 000 Osijek, Croatia
* Author to whom correspondence should be addressed.
Received: 27 May 2009; in revised form: 7 July 2009 / Accepted: 8 July 2009 / Published: 10 July 2009
Abstract: (7-Hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid methyl ester(1) upon reaction with ethyl bromoacetate furnishes (7-ethoxycarbonylmethoxy-2-oxo-2H-chromen-4-yl)-acetic acid methylester (2), which on treatment with 100% hydrazine hydrate yields (7-hydrazinocarbonylmethoxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide (3). The condensation of compound 3 with different aromatic aldehydes afforded a series of [7-(arylidenehydrazinocarbonylmethoxy)-2-oxo-2H-chromen-4-yl]-acetic acid arylidene-hydrazide Schiff’s bases 4a-k. Cyclo-condensation of compounds 4a-k with 2-mercapto-acetic acid in N,N-dimethylformamide in the presence of anhydrous ZnCl2 affordsN-(2-aryl-4-oxothiazolidin-3-yl)-2-(4-(2-aryl-4-oxothiazolidin-3-ylcarbamoyl)-methyl)-2-oxo-2H-chromen-7-yloxy)-acetamides 5a-k. Structure elucidation of the products has been accomplished on the basis of elemental analysis, IR, 1H-NMR and 13C-NMR data. Compounds 4a-k and 5a-k will be screened for their antibacterial activity against both Gram-positive and Gram-negative bacteria and the results reported elsewhere in due course.
Keywords: coumarin; dihydrazides; aromatic Schiff’s bases; N-(2-aryl-4-oxo-thiazolidin-3-yl)-2-((4-(2-aryl-4-oxo-thiazolidin-3-ylcarbamoyl)-methyl)-2-oxo-2H-chromen-7-yl- oxy)-acetamides; biological activity
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Cacic, M.; Molnar, M.; Balic, T.; Draca, N.; Rajkovic, V. Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid. Molecules 2009, 14, 2501-2513.
Cacic M, Molnar M, Balic T, Draca N, Rajkovic V. Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid. Molecules. 2009; 14(7):2501-2513.
Cacic, Milan; Molnar, Maja; Balic, Tomislav; Draca, Nela; Rajkovic, Valentina. 2009. "Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid." Molecules 14, no. 7: 2501-2513.