Azine関連化合物に関する研究(第4報) : ヘテロ環をもつAzine類の熱分解

概要

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2-Phenylacetylthiopheneketazine (Ia), 2-(Ib), 3-(Ic) and 4-phenacylpyridineketazine (Id) were pyrolyzed by a free radical process in order to obtain information concerning effect of heterocyclic rings on azine pyrolytic processes. The pyrolysis of Ia at 270° or 290° afforded principally ammonia, toluene, thiophenecarbonitrile and 3,5-dithienyl-4-phenylpyrazole (III), accompanied by lesser quantities of nitrogen, diphenylethane and an unidentified compound. The compound III was proved, by the investigation of the admixed melting point and infrared spectrum, to be identical with an authentic sample prepared from the reaction of 1-phenyl-1-thenoyl-2-thienylethylene with hydrazine. On the other hand, Ib and Id decomposed at 250° to afford nitrogen, ammonia and 2,5-diphenyl-3,4-di (α-pyridyl)-(VIIb) or 2,5-diphenyl-3,4-di (γ-pyridyl) pyrrole (VIId) as main products, accompanied by 1-or 4-picoline, benzonitrile and 3,5-diphenyl-4-(α-pyridyl) pyrazole (VIIIb) in small amounts. In the pyrolysis of Ic at the same temperature, however, 3-picoline, benzonitrile and 3,5-diphenyl-4-(β-pyridyl) pyrazole (VIIIc) were mainly formed, but nitrogen, ammonia and the corresponding pyrrole (VIIc) were formed in low yields. The structures of VII and VIII were confirmed by spectral studies as well as elemental analyses.
公益社団法人日本薬学会の論文
1969-06-25