Synthesis of novel bis-thiazoles, bis-thienopyridines, and bis-triazolothiadiazines linked to diphenyl ether core as novel hybrid molecules

Abstract

The reaction of the appropriate α-haloketones or α-keto-hydrazonoyl chlorides with the corresponding bis(hydrazinecarbothioamide) in EtOH at reflux in the presence of a few drops of TEA produced good yields of novel bis-thiazoles linked to diphenyl ether as novel hybrid molecules. Furthermore, some novel bis-thiazoles were obtained in high yields by reacting 1,1′-(oxybis(4,1-phenylene))bis(2-bromoethanone) with the appropriate thioamide. Furthermore, by reacting bis(2-bromoethanone) with the appropriate 4-amino-3-mercapto-1,2,4-triazole derivatives in ethanol in the presence of TEA, novel bis(5,6-dihydro-s-triazolo[3,4-b]thiadiazines) linked to diphenyl ether moiety were obtained in good yields. Moreover, by reacting bis(2-bromoethanone) with the appropriate pyridinethiones in ethanolic sodium ethoxide at reflux, good yields of bis(thienopyridines) linked to diphenyl ether moiety were obtained. The structures of new compounds were confirmed using elements and spectral data.

Graphical Abstract

Keywords:

• Bis(2-bromoethanone)
• bis(5,6-dihydro-s-triazolo[3,4-b]thiadiazines)
• bis-thiazoles
• bis(thienopyridines)
• diphenyl ether