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Abstract

An expeditious synthesis of series of novel 1,3,5-thiadiazine (5a-f) and (6a-f) derivatives have been described. These compounds were synthesized by reaction of 1-(N-((6-methyl-2-(p-tolyloxy)quinoline-3-yl)methylene)carbamimidoyl)-3-arylthiourea (3a-b) derivatives with N-aryl isocyanodichloride (4a-c) in chloroform followed by basification with dilute NH4OH to give the target compounds 5a-f; which were acetylated further to afford six novel 1,3,5-thiadiazin-3-(6H)-yl)ethanone (6a-f) derivatives. Synthesis of intermediate compounds 3a-b was obtained by reacting 6-methyl-2-(p-tolyloxy)quinoline-3-carbaldehyde (2a) and 1-carbamimidoyl-3-aryllthiourea (1a-b) in chloroform. Structures of compounds 5a-f and 6a-f were established by FTIR, 1H & 13C NMR, mass spectra and further supported by elemental analysis. All synthesized compounds were investigated for their in vitro antimicrobial screening against a panel of pathogenic microorganism comprising S. aureus as Gram positive while E. coli, P. vulgaris, S. typhi as Gram-negative bacterial strains.

Keywords

p-Tolyloxy quinoline-3-carbaldehyde Aryl imino 1,3,5-Thiadiazines Antimicrobial activity

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Idrees, M., J. Siddiqui, N., G. Bodkhe, Y., & Kola, S. (2020). Synthesis and Characterization of Novel 1,3,5-Thiadiazine Derivatives Integrated with Quinoline Moiety as Potent Antimicrobial Agents. Asian Journal of Organic & Medicinal Chemistry, 5(2), 149–155. https://doi.org/10.14233/ajomc.2020.AJOMC-P262
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