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 [1]

Article abstract of DOI:10.1002/jhet.5570300538

A series of 1,3-bis(1H-azol-1-yl)-2-aryl-2-propanols 17 were synthesized 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 methide in the presence of either 1,2,4-triazole or imidazole. The aromatic 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 benzoyl or 4-toluene- sulfonyl chloride to afford [4-(benzoyl or 4-toluenesulfonyl)amino]-4H- 1,2,4-triazole. Subsequent alkylations with 4-bromo- or 4-chlorophenacyl bromide produced 1-(4-bromo- or 4-chlorophenacyl)-4-[(benzoyl- or 4- toluenesulfonyl)amino]-1H-1,2,4-triazolium bromides. Neutralizations of these salts provided the corresponding ylides.