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.
引用
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页数:10
相关论文
共 52 条
[1]   Recent advances in the description of solvent effects with the polarizable continuum model [J].
Amovilli, C ;
Barone, V ;
Cammi, R ;
Cancès, E ;
Cossi, M ;
Mennucci, B ;
Pomelli, CS ;
Tomasi, J .
ADVANCES IN QUANTUM CHEMISTRY, VOL 32: QUANTUM SYSTEMS IN CHEMISTRY AND PHYSICS, PT II, 1998, 32 :227-261
[2]   Organocatalytic Enantioselective Synthesis of 1,4-Dihydropyridines [J].
Auria-Luna, Fernando ;
Marques-Lopez, Eugenia ;
Herrera, Raquel P. .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (13) :2161-2175
[3]   Cascade synthesis of 1,2-dihydropyridine from dienaminodioate and an imine: a three-component approach [J].
Challa, Chandrasekhar ;
John, Manju ;
Lankalapalli, Ravi S. .
TETRAHEDRON LETTERS, 2013, 54 (29) :3810-3812
[4]   Cardiovascular Calcium Channel Blockers: Historical Overview, Development and New Approaches in Design [J].
Drapak, Iryna ;
Perekhoda, Lina ;
Tsapko, Tetiana ;
Berezniakova, Natalia ;
Tsapko, Yevgen .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (04) :2117-2128
[5]   Dihydropyridines: evaluation of their current and future pharmacological applications [J].
Edraki, Najmeh ;
Mehdipour, Ahmad R. ;
Khoshneviszadeh, Mehdi ;
Miri, Ramin .
DRUG DISCOVERY TODAY, 2009, 14 (21-22) :1058-1066
[6]   Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: a combined experimental and DFT study [J].
Fan, Qiangwen ;
Tan, Hongbo ;
Li, Peng ;
Yan, Hong .
NEW JOURNAL OF CHEMISTRY, 2018, 42 (20) :16795-16805
[7]  
Frisch M J., 2009, Gaussian 09 revision d. 01, P106
[8]   THE PATH OF CHEMICAL-REACTIONS - THE IRC APPROACH [J].
FUKUI, K .
ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (12) :363-368
[9]   Template-Directed Photochemical [2+2] Cycloaddition in Crystalline Materials: A Useful Tool to Access Cyclobutane Derivatives [J].
Gan, Ming-Ming ;
Yu, Jian-Gang ;
Wang, Yao-Yu ;
Han, Ying-Feng .
CRYSTAL GROWTH & DESIGN, 2018, 18 (02) :553-565
[10]  
Glick S D, 2001, Alkaloids Chem Biol, V56, P39, DOI 10.1016/S0099-9598(01)56006-X