Iron Catalyzed [3+2] Cycloaddition of Tetrahydroisoquinoline: Synthesis of Dihydropyrrolo[2,1-a]isoquinolines

被引：12
|
作者：
Liu, Si-Wei [1 ,2 ]
Ma, Dan-Dan [1 ]
Zhu, Xin-Xin [1 ]
Luo, Cheng-Dan [1 ]
Tan, Hui-Lin [1 ]
Ju, Xiao-Li [1 ]
Tan, Xue [1 ]
Tang, Xiao-Hui [1 ]
Huang, Jie [1 ]
Wang, Jia [1 ]
Wang, Xian-Xun [2 ]
Cui, Hai-Lei [1 ]
机构：
[1] Chongqing Univ Arts & Sci, Lab Asymmetr Synth, 319 Honghe Ave, Chongqing 402160, Peoples R China
[2] Tonichem Pharmaceut Technol Co Ltd, Huizhou 516008, Peoples R China
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 9卷 / 10期
基金：
中国国家自然科学基金;
关键词：
Iron chloride; Dihydropyrrolo[2; 1-a]isoquinoline; Tetrahydroisoquinoline; Cycloaddition; Morita-Baylis-Hillman carbonate; BAYLIS-HILLMAN REACTION; EFFICIENT APPROACH; AZOMETHINE YLIDES; LAMELLARIN CORE; DERIVATIVES; CASCADE; CYCLIZATION; TANDEM; ANNULATION; REACTIVITY;
D O I：
10.1002/ajoc.202000211
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed an iron(III) chloride hexahydrate catalyzed formal [3+2] cycloaddition of tetrahydroisoquinolines with amide group-bearing Morita-Baylis-Hillman (MBH) carbonates. A range of highly functionalized dihydropyrrolo[2,1-a]isoquinolines could be prepared through SN2'/oxidation/electrocyclization/aromatization cascade (32-62% yield).
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页码：1617 / 1622
页数：6
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