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- Title
Catalytic N-formylation for synthesis of 6-substituted-2-benzothiazolylimino-5-piperazinyl-4-thiazolidinone antimicrobial agents.
- Authors
Patel, Rahul; Park, Se
- Abstract
A new class of piperazine-based 2-benzothiazolylimino-4-thiazolidinones has been efficiently prepared via highly accelerated N-formylation of N-isopropylpiperazine by the use of a mild heterogeneous catalyst, sulfated tungstate. Heterocyclization of N-(benzo[ d]thiazol-2-yl)-2-chloroacetamides ( 3a- j) by use of NHSCN in ethanol under reflux efficiently furnished the intermediates 2-benzothiazolyliminothiazolidin-4-ones ( 4a- j). These were treated with 4-isopropylpiperazine-1-carbaldehyde ( 2) to prepare the final products 5a- j. The structures of the new derivatives were confirmed by elemental analysis and use of spectroscopic data (FTIR and H NMR). Their pharmacological potential as promising antimicrobial agents was determined in vitro against bacteria and a fungus; the lowest minimum inhibitory concentrations (MIC) observed were in the range 4-8 µg/mL.
- Subjects
FORMYLATION; CATALYTIC activity; SUBSTITUTION reactions; ANTI-infective agents; PIPERAZINE
- Publication
Research on Chemical Intermediates, 2015, Vol 41, Issue 8, p5599
- ISSN
0922-6168
- Publication type
Article
- DOI
10.1007/s11164-014-1684-8