- Oxidative aromatization of 4,7-dihydro-6-nitroazolo[1,5-a] pyrimidines: Synthetic possibilities and limitations, mechanism of destruction, and the theoretical and experimental substantiation
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The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed.
- Balyakin, Ilya A.,Chupakhin, Oleg N.,Lyapustin, Daniil N.,Rusinov, Vladimir L.,Shchepochkin, Alexander V.,Ulomsky, Evgeny N.
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- Anodic Oxidation of Active Methylene Groups in the Presence of Excess Carboxylic Acid
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The anodic oxidation of anthrone, (9,(10H)-anthracenone), 9,10-dihydroanthracene and 1-tetralone in acetonitrile was studied under the presence of excess carboxylic acids.The oxidation of anthrone with acetic acid gave anthraquinone, 10-acetoxyanthrone and 10-methyl-10-acetoxyanthrone.A similar reaction of anthrone with propionic acid yielded 10-propionyloxyanthrone.The electronic oxidation of 9,10-dihydroanthracene yielded anthraquinone, anthrone, and 9-acetoxyanthrone under the same conditions.Also, 1-tetralone reacted with acetic acid and propionic acid at the 4 position of the carbonyl group, giving 4-acetoxy- and 4-propionyloxy-1-tetralone, respectively.
- Koketsu, Jugo,Kurita, Masasi,Tamano, Michiko,Fuijmura, Yoshikazu,Ando, Fumio
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p. 2767 - 2769
(2007/10/02)
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