新型区域选择性：不对称1,4-和1,2-二氢吡啶的三组分串联合成
Novel regioselectivity: three-component cascade synthesis of unsymmetrical 1,4- and 1,2-dihydropyridines.
作者信息
Wan Jie-Ping, Gan Shi-Feng, Sun Gong-Lei, Pan Yuan-Jiang
机构信息
Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.
出版信息
J Org Chem. 2009 Apr 3;74(7):2862-5. doi: 10.1021/jo900068z.
The three-component sequential reaction of alpha,beta-unsaturated aldehydes, amines, and enaminones proceeded smoothly to give 1,3,4-trisubstituted 1,4-dihydropyridines in aqueous DMF. Moreover, the unexpected regioselective formation of 1,2-dihydropyridines has been observed for the first time in such an approach. On the basis of a systematic study, the novel regioselectivity could be assigned both to steric and electronic effects originating from the amine partner.
α,β-不饱和醛、胺和烯胺酮的三组分连续反应在含水N,N-二甲基甲酰胺中顺利进行，生成1,3,4-三取代的1,4-二氢吡啶。此外，在这种方法中首次观察到了意外的区域选择性形成1,2-二氢吡啶。基于系统研究，这种新的区域选择性可归因于胺类反应物产生的空间和电子效应。
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