Regioselective photocycloaddition of pyridine derivatives to electron-rich alkenes

被引：7
|
作者：
Sakamoto, M
Sano, T
Fujita, S
Ando, M
Yamaguchi, K
Mino, T
Fujita, T
机构：
[1] Chiba Univ, Dept Mat Technol, Fac Engn, Inage Ku, Chiba 2638522, Japan
[2] Chiba Univ, Ctr Chem Anal, Inage Ku, Chiba 2638522, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 04期
关键词：
D O I：
10.1021/jo0266285
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Irradiation of a benzene solution of 3-cyano-2,6-dimethoxypyridine in the presence of ethyl vinyl ether (EVE) gave 1:1 photoadducts, 3-cyano-5-ethoxy-2,8-dimethoxy-4,5-dihydroazocine, in good yields, whose structure was established by X-ray single-crystal analysis. The photoadduct was produced via cycloaddition between the C3-C4 position of the pyridine derivatives and an alkene chromophore. On the other hand, 3-cyano-2,6-dimethoxy-4-methylpyridine cycloadds to EVE at the C2-C3 position of the pyridine ring upon irradiation. The difference is explained on the basis of the steric effect.
引用
收藏
页码：1447 / 1450
页数：4
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