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Molecules 2009, 14(7), 2501-2513; doi:10.3390/molecules14072501
Article

Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid

1,* , 1, 2, 1 and 3
1 Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhaca 20, 31 000 Osijek, Croatia 2 Department of Chemistry, J. J. Strossmayer University, Franje Kuhaca 20, 31 000 Osijek, Croatia 3 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 / Revised: 7 July 2009 / Accepted: 8 July 2009 / Published: 10 July 2009
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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 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.

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