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Synthesis of new series of N-3-[-{2-(substituted phenyl-4-oxo-5-(substituted benzylidene)-1,3-thiazolidine}-carbamyl]-propyl-2-aminothiazole and their biological importance

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Abstract

Synthesis of new series of N-3-[-{2-(substituted phenyl-4-oxo-5-(substituted benzylidene)-1,3-thiazolidine}-carbamyl]-propyl-2-aminothiazole, 5(a–s) have been developed. The cycloaddition reaction of thioglycolic acid with N-{3-(substituted benzylidine-carbamyl)-propyl}-2-aminothiazole, 3(a–s) in the presence of anhydrous ZnCl2 afforded new heterocyclic compounds N1-3-[-{2-(substituted phenyl-4-oxo-1,3-thiazolidine}-carbamyl]-propyl-2-aminothiazole 4(a–s). The latter product on treatment with several selected substituted aromatic aldehydes in the presence of C2H5ONa undergoes Knoevenagel reaction to yield 5(a–s). The structure of compounds 1, 2, 3(a–s), 4(a–s) and 5(a–s) were confirmed by IR, 1H NMR, 13C NMR, FAB mass and chemical analysis. All final compounds were screened for their antimicrobial activity against some selected bacteria and fungi and antituberculosis study against M. tuberculosis, gave acceptable activity.

A new series of N-3-[-{2-(substituted phenyl-4-oxo-5-(substituted benzylidene)-1,3-thiazolidine}-carbamyl]-propyl-2-aminothiazole, 5(a–s) have been synthesized from 2-aminothiazole. The structures of compounds were confirmed by spectroscopic and chemical methods. All the compounds were screened for their antimicrobial and antituberculosis activities.

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Authors and Affiliations

  1. Synthetic Organic Chemistry Laboratory, Department of Chemistry, Dr. H S Gour University (A Central University), Sagar, India, 470 003

    PUSHKAL SAMADHIYA, RITU SHARMA, SANTOSH K SRIVASTAVA & SAVITRI D SRIVASTAVA

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  1. PUSHKAL SAMADHIYA
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  2. RITU SHARMA
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  3. SANTOSH K SRIVASTAVA
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  4. SAVITRI D SRIVASTAVA
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Correspondence to PUSHKAL SAMADHIYA.

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SAMADHIYA, P., SHARMA, R., SRIVASTAVA, S.K. et al. Synthesis of new series of N-3-[-{2-(substituted phenyl-4-oxo-5-(substituted benzylidene)-1,3-thiazolidine}-carbamyl]-propyl-2-aminothiazole and their biological importance. J Chem Sci 123, 631–644 (2011). https://doi.org/10.1007/s12039-011-0123-2

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  • DOI: https://doi.org/10.1007/s12039-011-0123-2

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