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タイトル: Lactams. XXIII. Thermal cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system: Effect of an N-substituent
著者: Fujii, Tozo
Ohba, Masashi link image
Yoshifuji, Shigeyuki
Akiyama, Shigeaki
藤井, 澄三
大場, 正志
吉藤, 茂行
秋山, 茂明
発行日: 1985年 3月25日
出版社(者): 日本薬学会
雑誌名: Chemical & pharmaceutical bulletin
ISSN: 0009-2363
巻: 33
号: 3
開始ページ: 1062
終了ページ: 1068
キーワード: lactim ether synthesis
lactim ether alkylation
ester alkaline hydrolysis
lactam acid thermal cis-trans equilibration
lactam acid ^<13>C-NMR
^<13>C-NMR stereoisomer determination
抄録: In order to investigate the effect of an N-substituent on thermal cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system, the N-alkyl analogs (±)-1b, c and (±)-2b, c and the N-(2-arylethyl) analogs (-)-1f, g, i and (+)-2f, g, i were separately heated neat at 180℃, and the propress of their cis-trans isomerization reactions was followed by determining the isomer ratios in the reaction mixtures according to the previously reported C-13 nuclear magnetic resonance spectroscopic method. It has been found that in all cases the reaction comes to equilibrium within 28-130 min, when the cis and trans isomers exist in a ration of 1 : 2. These results together with those obtained previously with the analogs (±)-1a, d, e, (-)-1h, (±)-2a, d, e, and (+)-2h indicate that a higher and/or bulkier N-substituent tends to decrease the rate of cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system, which is a useful synthon for the synthesis of benzo-[a] quinolizidine-type Alangium alkaloids. Among the substrates used in the present equilibration study, (±)-1b, c and (±)-2b, c were prepared from the corresponding N-unsubstituted lactam esters (±)-3 and (±)-7 by the"lactim ether method."
URI: http://hdl.handle.net/2297/7628
資料種別: Journal Article
版表示: publisher
出現コレクション:2.査読済論文(薬)

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