2-アシルピリジン及び2-アシルキノリンのオキシムに関する研究

抄録

By the Grignard reaction of 2-cyano-pyridine and -quinoline, 2-acetyl-, 2-propionoyl-, and 2-benzoyl-pyridines and -quinolines, and 2-phenylacetylpyridine were synthesized. 2-Phenylacetylquinoline was obtained from ethyl quinaldate through 2-(α-cyanophenylacetyl) quinoline. 2-Phenacyl-pyridine and -quinoline come in four desmotropic forms of (A) C₅H₄N⋅CH₂COC₆H₅ or C₉H₆N⋅CH₂COC₆H₅ and (B) C₅H₄N⋅COCH₂C₆H₅ or C₉H₆N⋅COCH₂C₆H₅. The properties of these four compounds were compared with each product synthesized by the following two routes: (i) 2-Picoline or quinaldine → 2-styrylpyridine or -quinoline → dibromide → 2-(2-phenethinyl) pyridine or -quinoline → 2-phenacylpyridine or -quinoline. (ii) 2-Picoline or quinaldine → 2-picolyllithium or quinaldinyllithium → 2-phenacyl-pyridine or -quinoline. Each of the ketones was derived to the oxime and reaction with Fe²⁺ was carried out. The red to reddish violet complex formed with 2-acylpyridine was submitted to absorption spectral measurement to examine the effect of alkyl or aryl group of RCO-in the formation of a complex salt. It was found that C₅H₄N⋅CH₂C(=NOH)C₆H₅ and 2-acylquinolines do not form complex salt with Fe²⁺.