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

Molecules

Milan Cacic²  Maja Molnar²  Tomislav Balic¹  Nela Draca² 

[1] Department of Chemistry, J. J. Strossmayer University, Franje Kuhaca 20, 31 000 Osijek, Croatia;Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhaca 20, 31 000 Osijek, Croatia

关键词: coumarin;    dihydrazides;    aromatic Schiff’s bases;    N-(2-aryl-4-oxo-thiazolidin-3-yl)-2-((4-(2-aryl-4-oxo-thiazolidin-3-ylcarbamoyl)-methyl)-;    biological activity;   

DOI  :  10.3390/molecules14072501

来源: mdpi

【 摘 要 】

(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 affords N-(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.

【 授权许可】

CC BY   
© by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.