Lactams. XV. Chemistry of Unsaturated δ-Valerolactams

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概要

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• On the basis of chemical and spectroscopic evidence, the structure 5 has been assigned to an unsaturated lactam acid of mp 126-127° (slight effervescence) which was temporarily expressed by the structure 6 previously. The chemical evidence obtained here includes the results of the following reactions : esterifications of the lactam acid 5 to the ethyl ester 8 and to the methyl ester 9 ; alkaline hydrolyses of the two esters 8 and 9 to the starting acid 5 at room temperature ; conversion of 9 into the lactam amide 12 ; LiAlH_4 reduction of 9 to the lactam alcohol 10 ; chromic acid oxidation of 10 to the starting acid 5 ; alkaline hydrolyses of the esters 8 and 9 to a mixture of 5 and the isomeric lactam acid 7 at a higher temperature ; base-catalyzed isomerization of 5 to 7 or vice versa, reaching equilibrium ; thermal decarboxylation of 5 to a mixture of 13 and 14 ; base-catalyzed isomerization of 13 to 14. The assigned structures of the lactam derivatives thus obtained were also supported by their ultraviolet, infrared, proton magnetic resonance, and C-13 nuclear magnetic resonance spectra.

• 公益社団法人日本薬学会の論文
• 1979-08-25

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

• 古源 寛

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 古源 寛

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 伊賀 清美

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Yoshifuji Shigeyuki

  Faculty Of Pharmaceutical Sciences Of Hokuriku University

• 吉藤 茂行

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 伊賀 清美

  Faculty Of Pharmaceutical Sciences Kanazawa University

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