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

GRAPHICAL ABSTRACT

ABSTRACT

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 (¹H and ¹³C) 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.

KEYWORDS:

• Condensation
• chalcone
• thiazine
• thiophene
• thiourea

Funding

We are grateful to Al al-Bayt University (Mafraq, Jordan) and the DFG (Germany) for financial support.