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A new synthesis of 1‐aryl‐5‐cyano‐1 H ‐pyrazole‐4‐carboxylic acid, ethyl esters
Author(s) -
Beck James R.,
Ackmann Stephen A.,
Staszak Michael A.,
Wright Fred L.
Publication year - 1988
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.5570250348
Subject(s) - chemistry , pyrazole , thioether , aryl , sulfone , carboxylic acid , amine gas treating , organic chemistry , cyanide , alkyl
A novel conversion of 5‐amino‐1‐aryl‐1 H ‐pyrazole‐4‐carboxylic acid, ethyl esters to the corresponding 5‐cyano esters is described. The process involves nonaqueous diazotization of the amine to form the methyl thioether, which is oxidized to the methyl sulfone, which, in turn, is displaced by cyanide ion. The cyano esters are precursors to chemical hybridizing agents in wheat and barley.