Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives

Shankar Gaddeppa Alegaon; Kallanagouda Ramappa Alagawadi

doi:10.5155/eurjchem.2.1.94-99.161

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Published: Mar 28, 2011

DOI: https://doi.org/10.5155/eurjchem.2.1.94-99.161

Keywords:

Thiazolidinedione, Thiadiazole, Imidazo[2, 1-b][1, 3, 4]thiadiazoles, Antibacterial activity, Antifungal activity, Rhodanine

Section

Research Article

Issue

Vol. 2 No. 1 (2011): March 2011

Dates

Received 2010-06-09
Accepted 2010-10-11
Published 2011-03-28

Shankar Gaddeppa Alegaon

Department of Pharmaceutical Chemistry, Karnataka Lingayat Education University’s College of Pharmacy, Belgaum, Karnataka, IN-590010, India

Kallanagouda Ramappa Alagawadi

Department of Pharmaceutical Chemistry, Karnataka Lingayat Education University’s College of Pharmacy, Belgaum, Karnataka, IN-590010, India

Abstract

Imidazo[2,1-b][1,3,4]thiadiazoles (4a-g) were synthesized from 3,4,5-trimethoxy benzoic acid and thiosemicarbazide. Reaction of 4 with Vilsmeier-Haack reagent yielded imidazo [2,1-b][1,3,4] thiadiazole–5-carbaldehyde derivatives (5a-g). Obtained imidazo[2,1-b][1,3,4] thiadia zoles-5-carbaldehydes were subjected to Knoevenagel condensation with 2-(2,4-dioxothia zolidin-3-yl)acetic acid (1) and 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic (2) in the presence of catalytic amount of piperidine and acetic acid to afford imidazo[2,1-b][1,3,4]thiadiazoles (6a-g) and (7a-g), respectively. The structures of the newly synthesized compounds were confirmed by IR, NMR and elemental analyses. All compounds were screened for their antibacterial and antifungal activities. Some of the compounds displayed good antibacterial and antifungal activity.

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Alegaon, S. G.; Alagawadi, K. R. Synthesis, Characterization and Antimicrobial Activity Evaluation of New Imidazo [2,1-b][1,3,4]thiadiazole Derivatives. Eur. J. Chem. 2011, 2, 94-99.

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