Synthesis, characterization and antimicrobial activity of new chalcones and their 6-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine derivatives

Chalcones (5a-h) were prepared in high yields via the condensation of 3-acetyl-2,5-dichlorothiophene (3) with aryl aldehydes (4a-h). The reaction of the resulting chalcones with thiourea in the presence of a catalytic amount of hydrochloric acid provided the 1,3-thiazin-2-amine derivatives (6a-g) in...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2017-01, Vol.192 (5), p.560-564
Main Authors: Al-Refai, Mahmoud, Ibrahim, Mohammad M., Alsohaili, Sohail, Geyer, Armin
Format: Article
Language:English
Subjects:
Antimicrobial agents
chalcone
Condensation
thiazine
thiophene
thiourea
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Summary:Chalcones (5a-h) were prepared in high yields via the condensation of 3-acetyl-2,5-dichlorothiophene (3) with aryl aldehydes (4a-h). The reaction of the resulting chalcones with thiourea in the presence of a catalytic amount of hydrochloric acid provided the 1,3-thiazin-2-amine derivatives (6a-g) in moderate yields. All new compounds were characterized by extensive NMR analysis data, including 1D NMR experiments ( 1 H and 13 C) and 2D NMR experiments (COSY, HMBC, HSQC), as well as ESIMS and HRESIMS data. The newly synthesized compounds were evaluated for their biological activities, which demonstrate a very good to low bioactivities as antibacterial and antifungal, respectively.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426507.2016.1277526