Latams. X. The Alkaline Ferricyanide Oxidation of 3-Substituted 1-(3,4-Dimethoxyphenethyl) pyridinium Salts : Effects of Functional Substituents

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概要

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• In the alkaline ferricyanide oxidation at 32°of 3-substituted 1-(3,4-dimethoxyphenethyl) pyridinium bromides (type 3), the hydroxymethyl, N, N-dimethylaminomethyl, carbamoyl, and 1,1-ethylenedithioethyl groups at the 3-position have been found to orient the oxidation to both the 2-(type 4) and the 6-position (type 5) in ratios of 70 : 30,26 : 74,50 : 50,and 4 : 96. The carboxyl or 1,1-ethylenedioxyethyl group at the 3-position has oriented the oxidation to the 6-position exclusively, and possible factors in determining the regioselectivity in the ferricyanide oxidation of the 1,3-disubstituted pyridinium salts are discussed. For preparation of additional pyridone derivatives, 1-(3,4-dimethoxyphenethyl)-5-carboxy-2(1H)-pyridone (5d) was esterified with methanolic hydrogen chloride to the methyl ester (5h), and 1-(3,4-dimethoxyphenethyl)-5-(1,1-ethylenedioxyethyl)-2 (1H)-pyridone (5e) was converted into the methyl ketone (5i) by acid hydrolysis. The structures of the pyridones (4a, b, c, f, 5a-i) thus prepared have assigned on the basis of their ultraviolet, infrared, and nuclear magnetic resonance spectra.

• 1977-11-25

著者

• 吉藤 茂行

  Faculty Of Pharmaceutical Sciences Of Hokuriku University

• 桐沢 誠

  College of Pharmacy, Nihon University

• Ohba M

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 桐沢 誠

  College Of Pharmacy Nihon University

• 桐澤 誠

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• Yoshifuji Shigeyuki

  Faculty Of Pharmaceutical Sciences Of Hokuriku University

• 吉藤 茂行

  Faculty Of Pharmaceutical Sciences Hokuriku University

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