Synthesis and Antimicrobial Evaluation of Halogen-Containing Arylidene Thiazolo Triazinediones

Abstract

A series of 7-substituted arylidene-1,3-thiazolo[2,3-c]-1,2,4-triazine-4,6-diones were synthesized in an one-pot multicomponent reaction of 6-arylmethyl-3-mercapto-1,2,4-triazin-5-ones with substituted benzaldehydes and monochloroacetic acid in the presence of acetic anhydride, acetic acid, and sodium acetate. The structures of the new compounds were supported by IR, ¹H NMR, MS, and analytical data. All the new compounds were tested for their antibacterial and antifungal activity. Arylidene thiazolo triazinediones with 1,3-benzodioxolo substituent at seventh and p-chlorophenyl or 2,4-dichlorophenyl substituents at third displayed good antibacterial and antifungal activity. And also compound bearing 2,3,5-trimethoxyphenyl substituent at seventh and 2,4-dichlorophenyl substituent at third displayed good activity.

Keywords:

• Antibacterial
• antifungal activity
• arylidene thiazolo triazinediones
• one pot
• 1,2,4-triazin-5-ones

The authors are thankful to the Head, NMR Research Center, IISc-Bangalore, and CDRI, Lucknow, for providing ¹H NMR and mass spectral data. M.S.K. is grateful to CSIR New Delhi for providing Senior Research Fellowship.