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
[31]   Catalytic Enantioselective Azide-Alkyne Cycloaddition Chemistry Opens Up New Prospects for Chiral Triazole Syntheses [J].
Qin, Chang-Qing ;
Zhao, Cheng ;
Chen, Guo-Shu ;
Liu, Yun-Lin .
ACS CATALYSIS, 2023, 13 (09) :6301-6311
[32]   Transition Metal Vinylidene- and Allenylidene-Mediated Catalysis in Organic Synthesis [J].
Roh, Sang Weon ;
Choi, Kyoungmin ;
Lee, Chulbom .
CHEMICAL REVIEWS, 2019, 119 (06) :4293-4356
[33]  
Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO
[34]  
2-4
[35]   A highly efficient tandem [3+2] "click" cycloaddition/6-exo-cyclization strategy for the construction of triazole fused pyrazines [J].
Roy, Biswajit ;
Mondal, Debashis ;
Hatai, Joydev ;
Bandyopadhyay, Subhajit .
RSC ADVANCES, 2014, 4 (100) :56952-56956
[36]   Beyond click chemistry - supramolecular interactions of 1,2,3-triazoles [J].
Schulze, Benjamin ;
Schubert, Ulrich S. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2522-2571
[37]   Discovery of potent dipeptidyl peptidase IV inhibitors derived from β-aminoamides bearing substituted [1,2,3]-triazolopiperidines for the treatment of type 2 diabetes [J].
Shan, Zhenwei ;
Peng, Min ;
Fan, Houxing ;
Lu, Qingtao ;
Lu, Peng ;
Zhao, Chuansheng ;
Chen, Yilang .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (06) :1731-1735
[38]   Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution [J].
Shemet, Andrei ;
Carreira, Erick M. .
ORGANIC LETTERS, 2017, 19 (20) :5529-5532
[39]   One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds [J].
Song, Qiao ;
Liu, Yan ;
Cai, Linlin ;
Cao, Xinyu ;
Qian, Shan ;
Wang, Zhouyu .
CHINESE CHEMICAL LETTERS, 2021, 32 (05) :1713-1716
[40]   Synthesis of N-Fused Triazole-Piperazine-Quinazolinones via One-Pot Tandem Click Reaction and Cross-Dehydrogenative Coupling [J].
Srinath, Ravuri ;
Manna, Arindam ;
Shee, Subhankar ;
Pathi, Vijay Babu ;
Ghosh, Saswati ;
Khamaru, Krishnendu ;
Maiti, Nakul Chandra ;
Banerji, Biswadip .
ORGANIC LETTERS, 2021, 23 (24) :9365-9370