基于异源自分类串联反应集成策略构筑不对称的1,4-二氢吡啶衍生物  

Construction of Unsymmetrical 1,4-Dihydropyridines via Integration of Hetero-source Self-sorting Domino Reactions

作　　者：高蒙[1] 杨雁[1] 王紫华[1] 张冬雪[1] 吴柳明[1] 邓聪[1] 舒文明[1] 吴安心[1] 

机构地区：[1]华中师范大学化学学院农药与化学生物学教育部重点实验室,武汉430079

出　　处：《高等学校化学学报》2011年第9期2097-2102,共6页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:21032001;20872042);教育部创新团队基金(批准号:IRT0953);华中师范大学自主创新基金(批准号:2009007)资助

摘　　要：在假设不同结构的底物可同时参与自分类的串联反应,且各自生成的合适官能化的分子能进一步发生汇聚反应的基础上,建立了一个简单的反应模型,即在醋酸铵和间硝基苯甲醛的存在下,两种1,3-二羰基化合物经过2个并存的串联反应路径分别生成烯胺和烯酮中间体,二者随后汇聚选择性生成不对称的1,4-二氢吡啶.通过核磁共振直接检测反应液,进一步证实了该反应的高度选择性,即不同底物发生串联反应的高度自分类且汇聚的特性.On the hypothesis that hetero-sources could involve in self-sorting domino reactions and generate suitably functionalized intermediates to converge on the final product,we present herein a simple model of this strategy for the preparation of unsymmetrical 1,4-dihydropyridines.In the presence of CH3COONH4 and 3-nitrobenzaldehyde,two different 1,3-dicarbonyl compounds,respectively,generate the enamine and enone intermediates,which could finally combine with each other to efficiently afford the unsymmetrical 1,4-dihydropyridines.Direct 1H NMR analysis of the reaction mixture further proved the high selectivity of this reaction,which indicated the high self-sorting behavior of different domino reactions and their final convergent property.We anticipate that these results should inspire the design of more efficient domino reactions for the preparation of complex products from simple materials via integration of hetero-source self-sorting domino strategy.

关 键 词：异源自分类串联反应 Hantzsch反应 1 4-二氢吡啶 

分 类 号：O621[理学—有机化学]