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

高等学校化学学报 ›› 2011, Vol. 32 ›› Issue (9): 2097.

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

高蒙,杨雁,王紫华,张冬雪,吴柳明,邓聪,舒文明,吴安心

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

收稿日期:2011-04-22 修回日期:2011-06-30 出版日期:2011-09-10 发布日期:2011-08-11
通讯作者: 吴安心 E-mail:chwuax@mail.ccnu.edu.cn
基金资助:
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)和华中师范大学自主创新基金(批准号: 2009007)资助.

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

GAO Meng, YANG Yan, WANG Zi-Hua, ZHANG Dong-Xue, WU Liu-Ming, DENG Cong, SHU Wen-Ming, WU An-Xin*

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China

Received:2011-04-22 Revised:2011-06-30 Online:2011-09-10 Published:2011-08-11
Contact: WU An-Xin E-mail:chwuax@mail.ccnu.edu.cn
Supported by:
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)和华中师范大学自主创新基金(批准号: 2009007)资助.

摘要/Abstract

摘要： 假设不同结构的底物可以同时参与自分类的串联反应，而且各自生成的合适官能化的分子能够进一步发生汇聚反应，将更为有效地制备复杂的产物。在此基础上，我们建立了一个简单的反应模型来验证该策略的可行性。例如，在醋酸铵和间硝基苯甲醛的存在下，两种1,3-二羰基化合物可以经过两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.我们希望该结果能启发化学家通过更为有效的异源自分类串联反应集成策略实现由简单底物来高效制备复杂的分子.

关键词: 异源自分类串联反应; , Hantzsch反应; , 1,4-二氢吡啶

Abstract: 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.

Key words: Hetero-source self-sorting domino reaction, Hantzsch reaction, 1,4-Dihydropyridine

TrendMD:

高蒙杨雁王紫华张冬雪吴柳明邓聪舒文明吴安心. 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. 高等学校化学学报, 2011, 32(9): 2097.

GAO Meng, YANG Yan, WANG Zi-Hua, ZHANG Dong-Xue, WU Liu-Ming, DENG Cong, SHU Wen-Ming, WU An-Xin*. Construction of Unsymmetrical 1,4-Dihydropyridines via Integration of Hetero-source Self-sorting Domino Reactions. Chem. J. Chinese Universities, 2011, 32(9): 2097.