Lactams. IX. Generation of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Hydrocarbon Substituents at the 3-Position

フォーマット:

論文

責任表示:

Fujii, Tozo ; Yoshida, Kiyoshi ; Ohba, Masashi ; Yoshifuji, Shigeyuki

言語:

英語

出版情報:

日本薬学会, 1977-09-25

著者名:

• Fujii, Tozo
• Yoshida, Kiyoshi
• Ohba, Masashi
• Yoshifuji, Shigeyuki

掲載情報:

Chemical & pharmaceutical bulletin

ISSN:

0009-2363      

巻:

25

通号:

9

開始ページ:

2336

終了ページ:

2342

バージョン:

publisher

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 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. 続きを見る

URL:

http://hdl.handle.net/2297/7613