Visible light-catalyzed intermolecular [2+2] cycloaddition of 1,2-dihydropyridines: A combined experimental and DFT study

被引:1
作者
He, Yimeng [1 ]
Wang, Huiqin [1 ]
Yang, Yifan [1 ]
Yan, Hong [1 ]
机构
[1] Beijing Univ Technol, Fac Environm & Life, Beijing 100124, Peoples R China
基金
北京市自然科学基金;
关键词
1; 2-Dihydropyridines; 2+2] Cycloaddition reaction; Synthesis; Theoretical calculations; 1,4-DIHYDROPYRIDINES; PHOTOCYCLOADDITION; DERIVATIVES; DISCOVERY; OLEFINS; DESIGN; PATH; TOOL;
D O I
10.1016/j.tet.2023.133357
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this article, the intermolecular [2+2] cycloaddition of 1,2-dihydropyridines was achieved for the first time by visible light-catalyzed. A series of novel and complex cyclobutane derivatives, the dimers of diethyl 1,2-diaryl-1,2-dihydropyridine-3,5-dicarboxylate, were synthesized efficiently with visible light catalysts under the irradiation of blue LED lamps. The density functional theory and time-dependent density functional theory were used to elucidate the detailed reaction processes, such as the reaction mechanism and the stereoselectivity of cycloaddition products. (c) 2023 Published by Elsevier Ltd.
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页数:10
相关论文
共 52 条
[11]   Organophotocatalytic [2+2] Cycloaddition of Electron-Deficient Styrenes [J].
Golfmann, Maxim ;
Glagow, Louis ;
Giakoumidakis, Antonios ;
Golz, Christopher ;
Walker, Johannes C. L. .
CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (03)
[12]   AN IMPROVED ALGORITHM FOR REACTION-PATH FOLLOWING [J].
GONZALEZ, C ;
SCHLEGEL, HB .
JOURNAL OF CHEMICAL PHYSICS, 1989, 90 (04) :2154-2161
[13]   Half-Sandwich Iridium- and Rhodium-based Organometallic Architectures: Rational Design, Synthesis, Characterization, and Applications [J].
Han, Ying-Feng ;
Jin, Guo-Xin .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) :3571-3579
[14]   Glial cell line-derived neurotrophic factor mediates the desirable actions of the anti-addiction drug ibogaine against alcohol consumption [J].
He, DY ;
McGough, NNH ;
Ravindranathan, A ;
Jeanblanc, J ;
Logrip, ML ;
Phamluong, K ;
Janak, PH ;
Ron, D .
JOURNAL OF NEUROSCIENCE, 2005, 25 (03) :619-628
[15]   Visible light-catalyzed intermolecular [2+2] cycloaddition of 1,2-dihydropyridines: A combined experimental and DFT study [J].
He, Yimeng ;
Wang, Huiqin ;
Yang, Yifan ;
Yan, Hong .
TETRAHEDRON, 2023, 136
[16]   Discovery of substituted 1,4-dihydroquinolines as novel promising class of P-glycoprotein inhibitors: First structure-activity relationships and bioanalytical studies [J].
Hemmer, Marc ;
Krawczyk, Soeren ;
Simon, Ina ;
Hilgeroth, Andreas .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (15) :3005-3008
[17]   Crystal structure of a novel synthetic inhibitor of HIV-1 protease [J].
Hilgeroth, A ;
Tykarska, E ;
Jaskolski, M .
JOURNAL OF MOLECULAR STRUCTURE, 2002, 605 (01) :63-70
[18]   How cyclobutanes are assembled in nature - insights from quantum chemistry [J].
Hong, Young J. ;
Tantillo, Dean J. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (14) :5042-5050
[19]   Graphene/MoS2/FeCoNi(OH)x and Graphene/MoS2/FeCoNiPx multilayer-stacked vertical nanosheets on carbon fibers for highly efficient overall water splitting [J].
Ji, Xixi ;
Lin, Yanhong ;
Zeng, Jie ;
Ren, Zhonghua ;
Lin, Zijia ;
Mu, Yongbiao ;
Qiu, Yejun ;
Yu, Jie .
NATURE COMMUNICATIONS, 2021, 12 (01)
[20]  
Khan MOF, 2008, STUD NAT PROD CHEM, V34, P753