Three-Component Functionalized Dihydropyridine Synthesis via a Formal Inverse Electron-Demand Hetero-Diels-Alder Reaction

被引：39
|
作者：
Yan, Xiaonan [1 ]
Ling, Fei [1 ]
Zhang, Yuchen [1 ]
Ma, Cheng [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 14期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; SULFONYL AZIDE; LEWIS-ACID; CYCLOADDITION REACTIONS; YNAMIDES; DERIVATIVES; KETENIMINE; ALKYNES; 1,4-DIHYDROPYRIDINES; 1,2-DIAZINES;
D O I：
10.1021/acs.orglett.5b01622
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild three-component synthetic approach to versatile 2-amino-1,4-dihydropyridines from terminal alkynes, sulfonyl azides, and N-sulfonyl-1-aza-1,3-butadienes was successfully developed and relied on the in situ generation of metalated ynamide intermediates Ib to achieve a formal inverse electron-demand hetero-Diels-Alder reaction. Experimental results suggest that alkali Metal cations (Li+ and Cs+ ions) might play a critical role to achieve the cycloaddition process.
引用
收藏
页码：3536 / 3539
页数：4
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