Novel Regioselectivity: Three-Component Cascade Synthesis of Unsymmetrical 1,4-and 1,2-Dihydropyridines

作者:Wan Jie Ping; Gan Shi Feng; Sun Gong Lei; Pan Yuan Jiang*
来源:Journal of Organic Chemistry, 2009, 74(7): 2862-2865.
DOI:10.1021/jo900068z

摘要

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.