The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2+2] cycloaddition

被引：5
|
作者：
Chen, Xiu-Yu [1 ]
Zheng, Hui [1 ]
Han, Ying [1 ]
Sun, Jing [1 ]
Yan, Chao-Guo [1 ]
机构：
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 19卷
基金：
中国国家自然科学基金;
关键词：
1; 4-dihydropyridine; electron-withdrawing alkyne; formal [2+2] cycloaddition; Huisgen's 1; 4-dipole; isoquinoline; isoquinolino[1; 2-f][1; 6]naphthyridine; DIELS-ALDER REACTION; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; 3-COMPONENT REACTIONS; MOLECULAR DIVERSITY; CARBON-CARBON; CONSTRUCTION; 1,4-DIPOLES;
D O I：
10.3762/bjoc.19.73
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The three-component reaction of isoquinolines, dialkyl acetylenedicarboxylates, and 5,6-unsubstituted 1,4-dihydropyridines in acetonitrile at room temperature afforded functionalized isoquinolino[1,2-f][1,6]naphthyridines in good yields and with high dia-stereoselectivity. More importantly, the formal [2 + 2] cycloaddition reaction of dialkyl acetylenedicarboxylates and 5,6-unsubsti-tuted 1,4-dihydropyridines in refluxing acetonitrile gave unique 2-azabicyclo[4.2.0]octa-3,7-dienes as major products and 1,3a,4,6a-tetrahydrocyclopenta[b]pyrroles as minor products via further rearrangement.
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页码：982 / 990
页数：9
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