Cu/Ag-Mediated One-Pot Enantioselective Synthesis of Fully Decorated 1,2,3-Triazolo[1,5-a]pyrazines

被引:10
作者
Geng, Zi-Qi [1 ]
Zhao, Chunhui [1 ]
Qian, Hao-Dong [1 ]
Li, Si-Jia [1 ]
Peng, Hao [1 ]
Xu, Hao [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensing Technol &, CCNU uOttawa Joint Res Ctr,Key Lab Pesticides & Ch, 152 Luoyu Rd, Wuhan 430079, Peoples R China
基金
中国国家自然科学基金;
关键词
CLICK REACTION; CYCLOADDITION; AZIDE; BENZODIAZEPINE; BINDING; ALKYNES; ACCESS; ESTERS;
D O I
10.1021/acs.orglett.3c01524
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thesynthesis of chiral triazole-fused pyrazine scaffolds fromreadily available substrates in a step-economical asymmetric catalyticway is highly appealing. We herein report that an efficient Cu/Agrelay catalyzed protocol employing cascade asymmetric propargylicamination, hydroazidation, and [3 + 2] cycloaddition reaction withhigh efficiency to access the target enantioenriched 1,2,3-triazolo[1,5-a]pyrazine has been accomplished by applying a novel N,N,P-ligand. The one-potreaction of three components exhibits high functional group tolerance,excellent enantioselectivities, and a broad substrate scope with readilyavailable starting materials.
引用
收藏
页码:4504 / 4509
页数:6
相关论文
共 53 条
[1]   Tin(II) Chloride Catalyzed Multicomponent Synthesis of Propargylamines and Intramolecular [3+2] Cycloaddition [J].
Afraj, Shakil N. ;
Chen, Chinpiao .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (02) :257-263
[2]   1,2,3-triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors [J].
Bertelli, L ;
Biagi, G ;
Giorgi, I ;
Manera, C ;
Livi, O ;
Scartoni, V ;
Betti, L ;
Giannaccini, G ;
Trincavelli, L ;
Barili, PL .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (02) :113-122
[3]   New 1,2,3-triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors. II [J].
Biagi, G ;
Giorgi, I ;
Livi, O ;
Scartoni, V ;
Betti, L ;
Giannacini, G ;
Trincavelli, ML .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (07) :565-571
[4]   AgN3-Catalyzed Hydroazidation of Terminal Alkynes and Mechanistic Studies [J].
Cao, Shanshan ;
Ji, Qinghe ;
Li, Huaizhi ;
Pang, Maolin ;
Yuan, Haiyan ;
Zhang, Jingping ;
Bi, Xihe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (15) :7083-7091
[5]   A Facile Synthesis of 4,6,7,8,8a,9-Hexahydropyrrolo[1,2-a][1,2,3]triazolo[1,5-d]pyrazines by a Three-Component Coupling Reaction Followed by Intramolecular 1,3-Dipolar Cycloaddition [J].
Dhondge, Attrimuni P. ;
Afraj, Shakil N. ;
Nuzlia, Cut ;
Chen, Chinpiao ;
Lee, Gene-Hsian .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (19) :4119-4130
[6]   Palladium-Catalyzed Selective Three-Component Tandem Reaction to Bicyclic 1,2,3-Triazole Derivatives [J].
Duan, Xinyu ;
Huang, Xin ;
Fu, Chunling ;
Ma, Shengming .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) :627-647
[7]   α-Substituted vinyl azides: an emerging functionalized alkene [J].
Fu, Junkai ;
Zanoni, Giuseppe ;
Anderson, Edward A. ;
Bi, Xihe .
CHEMICAL SOCIETY REVIEWS, 2017, 46 (23) :7208-7228
[8]   Copper-Catalyzed Highly Enantioselective Difluoroalkylation of Secondary Propargyl Sulfonates with Difluoroenoxysilanes [J].
Gao, Xing ;
Cheng, Ran ;
Xiao, Yu-Lan ;
Wan, Xiao-Long ;
Zhang, Xingang .
CHEM, 2019, 5 (11) :2987-2999
[9]   Comprehensive Mechanistic Scenario for the Cu-Mediated Asymmetric Propargylic Sulfonylation Forging Tertiary Carbon Stereocenters [J].
Garcia-Roca, Aleria ;
Perez-Soto, Raul ;
Stoica, Georgiana ;
Benet-Buchholz, Jordi ;
Maseras, Feliu ;
Kleij, Arjan W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (11) :6442-6452
[10]   Propargylic Amination Enabled the Access to Enantioenriched Acyclic α-Quaternary α-Amino Ketones [J].
Guo, Wusheng ;
Zuo, Linhong ;
Cui, Manying ;
Yan, Biwei ;
Ni, Shaofei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (20) :7629-7634