Silver(I)- and Base-Mediated formal [4+3] Cycloaddition of in Situ generated 1,2-Diaza-1,3-dienes with C,N-Cyclic Azomethine Imines: An Efficient Protocol for the Synthesis of Tetrazepine Derivatives

被引：14
作者：
Li, Zefei [1 ]
Li, Shuaikang [1 ]
Kan, Tianjiao [1 ]
Wang, Xinyue [1 ]
Xin, Xin [1 ]
Hou, Yunlei [1 ]
Gong, Ping [1 ]
机构：
[1] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, 103 Wenhua Rd, Shenyang 110016, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 13期
关键词：
Silver; 1,2-Diaza-1,3-dienes; Azomethine imines; 4+3] Cycloaddition; Tetrazepine derivatives; SILVER(I)-RHODIUM(I) COOPERATIVE CATALYSIS; INTERMOLECULAR 5+2 CYCLOADDITION; GAMMA-SUBSTITUENT ALLENOATES; ALPHA-HALOGENO HYDRAZONES; RING-CLOSURE REACTIONS; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; TANDEM REACTION; SULFUR YLIDES;
D O I：
10.1002/adsc.202000398
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A silver(I)- and base-mediated formal [4+3] cycloaddition reaction of in situ generated 1,2-diaza-1,3-dienes with in situ formed C,N-cyclic azomethine imines has been developed. This protocol provided an efficient method for the synthesis of biologically important 1,2,4,5-tetrazepine derivatives with a wild substrate scope and excellent functional group tolerance in moderate to excellent yields.
引用
收藏
页码：2626 / 2631
页数：6
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共 97 条
[71]   Copper-catalyzed radical Heck type cyclization: a three-component reaction of DABCO•(SO2)2, aryldiazonium tetrafluoroborates and dienes toward sulfonated benzo- seven-membered nitrogen heterocycles [J].
Wang, Hepan ;
Wang, Bingbing ;
Sun, Song ;
Cheng, Jiang .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (17) :2547-2551
[72]   Asymmetric Synthesis of Spirobenzazepinones with Atroposelectivity and Spiro-1,2-Diazepinones by NHC-Catalyzed [3+4] Annulation Reactions [J].
Wang, Lei ;
Li, Sun ;
Bluemel, Marcus ;
Philipps, Arne R. ;
Wang, Ai ;
Puttreddy, Rakesh ;
Rissanen, Kari ;
Enders, Dieter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) :11110-11114
[73]   N-Alkylation-Initiated Redox-Neutral [5+2] Annulation of 3-Alkylindoles with o-Aminobenzaldehydes: Access to Indole-1,2-Fused 1,4-Benzodiazepines [J].
Wang, Shuai ;
Shen, Yao-Bin ;
Li, Long-Fei ;
Qiu, Bin ;
Yu, Liping ;
Liu, Qing ;
Xiao, Jian .
ORGANIC LETTERS, 2019, 21 (22) :8904-8908
[74]   Hydride transfer initiated ring expansion of pyrrolidines toward highly functionalized tetrahydro-1-benzazepines [J].
Wang, Shuai ;
An, Xiao-De ;
Li, Shuai-Shuai ;
Liu, Xicheng ;
Liu, Qing ;
Xiao, Jian .
CHEMICAL COMMUNICATIONS, 2018, 54 (98) :13833-13836
[75]   Synthesis of 5-(Trifluoromethyl)pyrazolines by Formal [4+1]-Annulation of Fluorinated Sulfur Ylides and Azoalkenes [J].
Wang, Zhiyong ;
Yang, Yanzhou ;
Gao, Fang ;
Wang, ZZhiyong ;
Luo, Qian ;
Fang, Ling .
ORGANIC LETTERS, 2018, 20 (04) :934-937
[76]   Enantioselective synthesis of multi-nitrogen-containing heterocycles using azoalkenes as key intermediates [J].
Wei, Liang ;
Shen, Chong ;
Hu, Yuan-Zhen ;
Tao, Hai-Yan ;
Wang, Chun-Jiang .
CHEMICAL COMMUNICATIONS, 2019, 55 (47) :6672-6684
[77]   Catalytic asymmetric inverse electron demand Diels-Alder reaction of fulvenes with azoalkenes [J].
Wei, Liang ;
Zhu, Qiao ;
Song, Zhi-Min ;
Liu, Kang ;
Wang, Chun-Jiang .
CHEMICAL COMMUNICATIONS, 2018, 54 (20) :2506-2509
[78]   Copper(II)-Catalyzed Asymmetric 1,3-Dipolar [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines with Azoalkenes [J].
Wei, Liang ;
Wang, Zuo-Fei ;
Yao, Lu ;
Qiu, Guofu ;
Tao, Haiyan ;
Li, Hua ;
Wang, Chun-Jiang .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (24) :3955-3959
[79]   Copper(I)-Catalyzed Asymmetric 1,3-Dipolar [3+4]Cycloaddition of Nitrones with Azoalkenes [J].
Wei, Liang ;
Yao, Lu ;
Wang, Zuo-Fei ;
Li, Hua ;
Tao, Hai-Yan ;
Wang, Chun-Jiang .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) :3748-3752
[80]   Silver Triflate-Palladium Chloride Cooperative Catalysis in a Tandem Reaction for the Synthesis of H-Pyrazolo[5,1-a]isoquinolines [J].
Xiao, Qing ;
Sheng, Jie ;
Ding, Qiuping ;
Wu, Jie .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) :2321-2326
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