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

页码：1447 / 1450

页数：4

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