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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. [ABSTRACT FROM AUTHOR]

A synthesis of novel bis( s-triazolo[3,4- b][1,3,4]thiadiazines) 4, 5, 6 in which the triazolothiadiazine is linked to the benzene core through the thiadiazine ring via phenoxymethyl spacers was reported. First attempt to synthesize 4, 5, 6 by the reaction of the appropriate bis(acetophenones) with 4-amino-3-mercapto-1,2,4-triazole derivatives using an acidified method were unsuccessful. On the other hand, reaction of the corresponding bis( α-bromoketones) with 4-amino-3-mercapto-1,2,4-triazole derivatives afforded 4, 5, 6 in good yields. The reaction pathway is assumed to involve to give bis(aminotriazole) intermediates, followed by to give 4, 5, 6. The successful isolation of the corresponding bis(aminotriazole) intermediates provides strong evidence for the proposed mechanism. The novel bis(thiazoles) 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, linked to alkyl or aryl spacers can also be synthesized by reaction of the appropriate bis(bromoacetyl) compounds 12a, 12b, 12c and 14, 15, 16, 17, 18, 19 with the corresponding thioamide derivatives 20, 21, 22. [ABSTRACT FROM AUTHOR]