Lactams. VIII. The Alkaline Ferricyanide Oxidation of 3-Substituted 1-(3,4-Dimethoxyphenethyl) pyridinium Salts : Effects of Hydrocarbon Substituents on Orientation of the Oxidation

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概要

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• The alkaline ferricyanide oxidation at 32°of 1-(3,4-dimethoxyphenethyl) pyridinium bromides (3c-f) carrying the n-butyl, 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.

• 1977-08-25

著者

• 吉藤 茂行

  Faculty of Pharmaceutical Sciences, Hokuriku University

• 藤井 澄三

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 吉藤 茂行

  Faculty Of Pharmaceutical Sciences Of Hokuriku University

• 桐沢 誠

  College of Pharmacy, Nihon University

• 吉田 清史

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Ohba M

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 三口 守公

  Research Center Taisho Pharmaceutical Co. Ltd.

• 桐沢 誠

  College Of Pharmacy Nihon University

• 桐沢 誠

  Pharmaceutical Institute, College of Science and Engineering, Nihon University

• Yoshifuji Shigeyuki

  Faculty Of Pharmaceutical Sciences Of Hokuriku University

• 桐沢 誠

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• 吉藤 茂行

  Faculty Of Pharmaceutical Sciences Hokuriku University

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