A significant substituent effect on the regioselectivity in addition of alkynes to 3-substituted pyridines

被引：13
|
作者：
Yamada, Shinji [1 ]
Toshimitsu, Aya [1 ]
Takahashi, Yasuko [1 ]
机构：
[1] Ochanomizu Univ, Dept Chem, Fac Sci, Bunkyo Ku, Tokyo 1128610, Japan
来源：
TETRAHEDRON | 2009年 / 65卷 / 11期
基金：
日本学术振兴会;
关键词：
STEREOSELECTIVE SYNTHESIS; GRIGNARD-REAGENTS; DERIVATIVES; DIHYDROPYRIDINES; SALTS; 1,4-DIHYDROPYRIDINES; PIPERIDINES; CHEMISTRY; ACID; PI;
D O I：
10.1016/j.tet.2009.01.022
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A substituent at the 3-position on a pyridine ring significantly affects the regioselectivity during the addition of alkynes to pyridinium salts. When the substituent is an electron-withdrawing group, 1,6-adducts are predominantly produced, whereas, 1,2-adducts become the major products when the substituent is an electron-donating group. The changes in the regioselectivity depending on the substituent can be explained by the difference in the product stabilities. The produced dihydropyridines are easily aromatized into disubstituted pyridines with chloranil in quantitative yields. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2329 / 2333
页数：5
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