Studies on the N-Oxides of π-Deficient N-Heteroaromatics. XXXVI. Photochemical and Thermal Michael Reactions of Alcohols with Methyl 2-Phenyl-3, 1-benzoxazepine-5-carboxylate and Its Derivatives

フォーマット:

論文

責任表示:

Kaneko, Chikara ; Fujii, Harue ; Kawai, Shinji ; Hashiba, Kazuhiko ; Karasawa, Yoshio ; Wakai, Masue ; Hayashi, Reiko ; Somei, Masanori

言語:

英語

出版情報:

Pharmaceutical Society of Japan = 日本薬学会, 1982-01-01

著者名:

Kaneko, Chikara

Fujii, Harue

Kawai, Shinji

Hashiba, Kazuhiko

Karasawa, Yoshio

Wakai, Masue

Hayashi, Reiko

Somei, Masanori

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掲載情報:

Chemical and Pharmaceutical Bulletin

ISSN:

0009-2363      

巻:

30

通号:

1

開始ページ:

74

終了ページ:

85

バージョン:

publisher

概要:

Irradiation (≥300 nm) of methyl 2-phenyl-3, 1-benzoxazepine-5-carboxylate in an alcohol afforded the Z-isomer of methyl 3-alkoxy-2-(2-benzamidophenyl)-acrylate as the major addition product. In contrast, thermal reaction of the oxazepine with a primary alcohol in the presence of triethylamine led to the exclusive formation of the corresponding E-isomer. The same kinds of Michael addition products were also obtained … stereoselectively from 3, 1-benzoxazepines having an acetyl group at the 5-position under these conditions. The interrelation between the stereoisomers obtained from the oxazepine and an alcohol under these two conditions was established by photochemical equilibration, and the stereochemistry of the two isomers was determined by proton magnetic resonance spectroscopy. An explanation is proposed for the observed stereoselectivities in the two kinds (photochemical and thermal) of reactions. 続きを見る

URL:

http://hdl.handle.net/2297/44026