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| 1.
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論文
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Fujii, Tozo ; Yoshifuji, Shigeyuki ; Yoshida, Kiyoshi ; Ohba, Masashi ; Ikegami, Shiro ; Kirisawa, Makoto
概要:
The alkaline ferricyanide oxidation of the quaternary pyridinium salts (Ia-g) furnished pairs of the isomeric 2-pyridones (IIa-g) and 6-pyridones (IIIa-g) in good total yields. In all cases, the oxidation at the 2-position was much
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favored over that at the 6-position. The effect of the aryl group in the N-aralkyl chain on the orientation of the oxidation seemed to be negligibly small regardless of the number of the methylene groups separating the aryl group from the nitrogen. The extent of the 6-oxidation was slightly increased as the alkyl group at the 3-position was changed from the methyl to the ethyl group. The nuclear magnetic resonance spectra of these pyridones were measured in deuteriochloroform, carbon tetrachloride, and benzene-d_6. On the basis of the results summarized in Tables III-VI, the effects of the aryl group and the number of the methylene groups in the N-substituent on the chemical shifts for the pyridone-ring and neighboring group protons are discussed.
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| 2.
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Fujii, Tozo ; Yoshifuji, Shigeyuki ; Hatanaka, Yasumaru ; Yoshida, Kiyoshi ; Ohba, Masashi ; Yamada, Koichiro ; Ohkuma, Mihoko ; Shinoda, Hirotaka ; Mizuno, Denichi
概要:
Seventy-four compounds related to lactams and pyridones were synthesized and their anti-tumor activity was examined using Ehrlich carcinoma cells. 4-(2-Piperidyl) butyric acid hydrochloride was found to have some anti-tumor
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effect on the solid type of Ehrlich carcinoma cells, but no other substances were found to be effective. Correlation between the anti-tumor activity and structure of the tested compounds still remains uncertain.
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| 3.
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Fujii, Tozo ; Yoshida, Kiyoshi ; Ohba, Masashi ; Yoshifuji, Shigeyuki
概要:
The mercuric acetate-(ethylenedinitrilo) tetraacetic acid oxidation of 1-(3,4-dimethoxyphenyl)-2-(3-substituted piperidino) ethanols (7c-f), which carry the n-butyl, isopropyl, benzyl, and phenyl group as the 3-substituent in
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the piperidine ring, has been found to produce the corresponding 2- (8c-f) and 6-piperidones (12c-f) in good yields in ratios of 41 : 59,29 : 71,26 : 74,and 15 : 85. It is suggested that the 3-substituents exert both steric and electronic effects. The structures of the lactam alcohols (8c-f, 12c-f) have been confirmed by the chemical correlation with the known pyridones (11c-f, 15c-f) through the lactams (10c-f, 14c-f). The starting piperidinoethanols (7c-f) have been synthesized from the 3-substituted pyridines (5c-f) by quaternization with 3,4-dimethoxyphenacyl bromide followed by catalytic and sodium borohydride reductions.
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| 4.
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論文
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Fujii, Tozo ; Yoshida, Kiyoshi ; Ohba, Masashi ; Mitsukuchi, Morihiro ; Tanaka, Izumi ; Yoshifuji, Shigeyuki ; Kirisawa, Makoto
概要:
The alkaline ferricyanide oxidation at 32°of 1-(3,4-dimethoxyphenethyl) pyridinium bromides (3c-f) carrying the n-butyl,
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isopropyl, benzyl, and phenyl group at the 3-position has been found to produce the corresponding 2-(4c-f) and 6-pyridones (5c-f) in ratios of 74 : 26,71 : 29,69 : 31,and 13 : 87. In the case of the 3-benzyl derivative (3e), 1-(3,4-dimethoxyphenethyl)-5-benzoyl-2 (1H)-pyridone (5g) has also been obtained in 1% yield. On the basis of the present and earlier data, possible factors in determining the orientation in the ferricyanide oxidation of 1,3-disubstituted pyridinium salts are discussed.
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| 5.
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論文
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Fujii, Tozo ; Hiraga, Takashi ; Yoshifuji, Shigeyuki ; Ohba, Masashi ; Yoshida, Kiyoshi
概要:
3-tert-Butylpyridine (11) has been synthesized from neopentyl alcohol in 16% overall yield through a five-step sequence.
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Among the steps involved are the cycloaddition of α-tert-butylacrolein (9) to butyl vinyl ether and conversion of the resulting dihydropyran derivative (10) into the pyridine base (11).
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