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7654

SYNTHESIS, REACTIONS, AND ANTI-BACTERIAL ACTIVITY OF SOME NEW N-BENZYL-4-OXOTHIAZOLIDIN-2-YLIDENE)ACETAMIDE DERIVATIVES

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Last updated: 03 Jan 2025

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Chemistry

Abstract

Treatment of N-benzyl-2-cyanoacetamide (1) with ethyl isothiocyanate (2) and p-phenylenediisothiocyanate (11) gave the non-isolable intermediates 3 and 12, respectively. Subsequent treatment of 3 and 12, respectively with α-halo esters and/or chloroacetone gave the corresponding 4-oxothiazolidin-2-ylidene 5a-c, bis(4-oxothiazolidin-2-ylidene) (14), thiazol-2-ylidene (6) and bis(5-acetyl-4-amino-3-N-benzylthiophenecarboxamido)-1-,4-pheneylenediamine (13) derivatives, respectively. Reaction of 5a with electrophilic carbon was studied where derivatives (8a,b), 10 were obtained. Cyclocondensation of 1 with thioglycolic acid afforded thiazolidin-4-one derivative (15). Condensation of 15 with 1-naphthaldehyde, arylidenemalononitriles and ethyl α-cyanocinnamate gave 4,5-dihydro-thiazol-2-ylacrylamide (17), thiazolo[3,2-a]pyridines (16a,b) and (18), respectively. The structures of these new compounds were confirmed by IR, (1H- and 13C-NMR) and mass spectral analyses. Some of the synthesized compounds were tested in vitro for their antimicrobial activity, where compounds 5a, 6, 8b, 16a, 16b, and 17 exhibited the best anti-bacterial activity against Salmonella typhi NCIM130331.

DOI

10.21608/absb.2009.7654

Keywords

N-benzyl-2-cyanoacetamide, thiazolidinone, bisthiazoli-dinone derivatives

Volume

20

Article Issue

Issue 2-A

Related Issue

1473

Issue Date

2009-12-01

Receive Date

2009-07-14

Publish Date

2009-12-18

Page Start

75

Page End

88

Print ISSN

1110-2535

Online ISSN

2636-3305

Article File

ABSB_Volume 20_Issue Issue 2-A_Pages 75-88.pdf

PDF . 149.7kB

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https://absb.journals.ekb.eg/article_7654.html

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https://absb.journals.ekb.eg/service?article_code=7654

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Original Article

Type Code

520

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Journal

Publication Title

Al-Azhar Bulletin of Science

Publication Link

https://absb.journals.ekb.eg/

MainTitle

SYNTHESIS, REACTIONS, AND ANTI-BACTERIAL ACTIVITY OF SOME NEW N-BENZYL-4-OXOTHIAZOLIDIN-2-YLIDENE)ACETAMIDE DERIVATIVES

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Article

Created At

22 Jan 2023