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Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid
(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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Molecular Diversity Preservation International
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255314/ https://www.ncbi.nlm.nih.gov/pubmed/19633619 http://dx.doi.org/10.3390/molecules14072501 |
Sumario: | (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 ZnCl(2) 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, (1)H-NMR and (13)C-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. |
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