Reactions of azomethine derivatives. IV. The synthesis of 2,3,5-trisubstituted 2-pyrrolin-4-ones and their oxidation to 2,4,5-trisubstituted 1,3-oxazin-6-ones.
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概要
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The reaction of aromatic azines with diphenylcyclopropenone in refluxing toluene gave 5-aryl-2,3-diphenyl-2-pyrrolin-4-ones (<B>4</B>) in moderate yields <I>via</I> initial [2+3] 1:1 cycloaddition and subsequent elimination of an aromatic nitrile from the adducts. Treatment with phosphorus pentasulfide deoxygenated the compounds <B>4</B> to 5-aryl-2,3-diphenyl-pyrroles. The same compounds <B>4</B> were oxidized to 2-aryl-4,5-diphenyl-1,3-oxazin-6-ones (<B>11</B>) by refluxing the pyridine solution in a stream of oxygen, by treatment with hydrogen peroxide, or by irradiation of the chloroform solution in a stream of oxygen. Treatment with alkali in aqueous pyridine converted <B>4</B> into 3-aroylamino-2,3-diphenylacrylic acids. These were also obtained from the hydrolysis of <B>11</B>. When <I>p</I>-dimethylaminobenzaldehyde azine reacted with diethyl azodicarboxylate in refluxing toluene, a 1:2 conjugated adduct, 3,6-bis(<I>p</I>-dimethylaminophenyl)-1,2,7,8-tetrakis(ethoxycarbonyl)-1,2,4,5,7,8-hexaaza-3,5-octadiene, and a 1:1 conjugate adduct, 3,6-bis <I>p</I>(-dimethylaminophenyl)-1,2-bis(ethoxycarbonyl)-1,2,4,5-tetraaza-3,5-hexadiene, were obtained.
- 公益社団法人 日本化学会の論文
著者
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Watanabe Shin-ichi
Department Of Chemistry Faculty Of Science Hiroshima University
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Takahashi Masahiko
Department Of Anesthesiology And Emergency Medicine Tohoku University Postgraduate Medical School
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Inaba Nobuyuki
Department of Industrial Chemistry, Faculty of Engineering, Ibaraki University
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Kirihara Hiroji
Department of Industrial Chemistry, Faculty of Engineering, Ibaraki University
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Watanabe Shin-ichi
Department of Industrial Chemistry, Faculty of Engineering, Ibaraki University
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