Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinoline and Ethyl (Z)-3-Acetoxy-3-tosylpent-4-enoate through Tertiary-Amine-Catalyzed [3+2] Annulation

被引：23
|
作者：
Lei, Yu [1 ]
Xing, Jiao-Jiao [1 ]
Xu, Qin [1 ]
Shi, Min [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[3] East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 21期
基金：
中国国家自然科学基金; 以色列科学基金会;
关键词：
Amines; Annulation; Azo compounds; Nitrogen heterocycles; Synthetic methods; C; N-CYCLIC AZOMETHINE IMINES; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; BAYLIS-HILLMAN REACTIONS; DNA GYRASE INHIBITORS; ANTIBACTERIAL ACTIVITY; BIOLOGICAL EVALUATION; ALPHA; BETA-UNSATURATED ALDEHYDES; ANTIMICROBIAL AGENTS; ALLENIC ESTERS; FACILE ACCESS;
D O I：
10.1002/ejoc.201600577
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed divergent [3+2] annulation of C,N-cyclic azomethine imines with -acetoxyallenoates was developed; 5,6-dihydropyrazolo[5,1-a]isoquinolines and ethyl (Z)-3-acetoxy-3-tosylpent-4-enoates were afforded in moderate to good yields in a one-pot manner under mild conditions. This annulation reaction provides a highly efficient method to construct dinitrogen-fused heterocycles and ethyl (Z)-3-acetoxy-3-tosylpent-4-enoates at the same time.
引用
收藏
页码：3486 / 3490
页数：5
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