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Conversion of 4‐amino‐4 H ‐1,2,4‐triazole to 1,3‐bis(1 H ‐azol‐l‐yl)‐2‐aryl‐2‐propanols and 1‐phenacyl‐4‐[(benzoyl or 4‐toluenesulfonyl)‐imino]‐(1 H ‐1,2,4‐triazolium) Ylides
Author(s) -
Narayanan Anjana,
Chapman David R.,
Upadhyaya Subhash P.,
Bauer Ludwig
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300538
Subject(s) - chemistry , benzoyl chloride , sulfonyl , aryl , bromide , phenacyl bromide , phenacyl , medicinal chemistry , imidazole , toluene , triazole , 1,2,3 triazole , stereochemistry , organic chemistry , alkyl
A series of 1,3‐bis(1 H ‐azol‐1‐yl)‐2‐aryl‐2‐propanols 17 were synthesized in an one‐pot procedure by reacting l‐aryl‐2‐(1 H ‐1,2,4‐triazol‐l‐yl)‐ or l‐aryl‐2‐(1 H ‐imidazol‐l‐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‐4 H ‐1,2,4‐triazole was acylated with either benzoyl or 4‐toluene‐sulfonyl chloride to afford [4‐(benzoyl or 4‐toluenesulfonyl)amino]4 H ‐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]‐1 H ‐1,2,4‐triazolium bromides. Neutralizations of these salts provided the corresponding ylides.