CONVERSION OF 4-AMINO-4H-1,2,4-TRIAZOLE TO 1,3-BIS(1H-AZOL-1-YL)2-ARYL-2-PROPANOLS AND 1-PHENACYL-4-[(BENZOYL OR 4-TOLUENESULFONYL)IMINO]-(1H-1,2,4-TRIAZOLIUM) YLIDES

A series of 1,3-bis(1H-azol-1-yl)-2-aryl-2-propanols 17 were synthesiz ed in an one-pot procedure by reacting 1-aryl-2-(1H-1,2,4-triazol-1-yl )- or 1-aryl-2-(1H-imidazol-1-yl)ethanones with dimethylsulfoxonium me thide in the presence of either 1,2,4-triazole or imidazole. The aroma tic groups in 17 were either 4-bromo-, 4-chloro-, 2,4-dichloro- or 2,4 -difluorophenyl. 4-Amino-4H-1,2,4-triazole was acylated with either be nzoyl or 4-toluene-sulfonyl chloride to afford [4-(benzoyl or 4-toluen esulfonyl)amino]-4H-1,2,4-triazole. Subsequent alkylations with 4-brom o- or 4-chlorophenacyl bromide produced 1-(4-bromo- or 4-chlorophenacy l)-4-[(benzoyl- or 4-toluenesulfonyl)amino]- 1H-1,2,4-triazolium bromi des. Neutralizations of these salts provided the corresponding ylides.