Direct Irradiation of (E)-Styrylpyridin-2(1H)-ones to (Z)-Isomers with Visible Light

被引:2
作者
Sui, Jingzhi [1 ,2 ]
Li, Miaoran [1 ,2 ]
Zhang, Zihan [1 ,2 ]
Liang, Yong [1 ,2 ,3 ]
Wang, Tao [1 ,2 ]
Zhang, Zunting [1 ,2 ]
机构
[1] Shaanxi Normal Univ, Key Lab, Natl Engn Lab Resource Dev Endangered Crude Drugsi, Minist Educ Med Resources & Nat Pharmaceut Chem, Xian 710119, Peoples R China
[2] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710119, Peoples R China
[3] Beckman Res Inst City Hope, Dept Mol Med, Duarte, CA 91010 USA
基金
中国国家自然科学基金;
关键词
direct irradiation; olefin isomerization; styrylpyridin-2(1H)-ones; visible light; Z ISOMERIZATION; Z-ALKENES; RESVERATROL; OLEFINATION; PALLADIUM; DISCOVERY; STILBENE;
D O I
10.1002/ajoc.202200701
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The E to Z isomerization of styrylpyridin-2(1H)-ones was achieved through visible light (420 nm) irradiation in dioxane at ambient temperature. Driven by the visible light, (E)-3-styrylpyridin-2(1H)-ones, (E)-4-styrylpyridin-2(1H)-ones and (E)-5-styrylpyridin-2(1H)-ones in dioxane at room temperature under Argon atmosphere were successfully converted to the corresponding (Z)-styrylpyridin-2(1H)-ones in good yields. The described E to Z photoisomerization of styrylpyridin-2(1H)-ones proceeded smoothly with the 420 nm blue light, avoided usage of photocatalysts, additives and are easy to operate.
引用
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页数:4
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共 30 条
[1]   Resveratrol: A review of preclinical studies for human cancer prevention [J].
Athar, Mohammad ;
Back, Jung Ho ;
Tang, Xmwel ;
Kim, Kwang Ho ;
Kopelovich, Levy ;
Bickers, David R. ;
Kim, Arianna L. .
TOXICOLOGY AND APPLIED PHARMACOLOGY, 2007, 224 (03) :274-283
[2]   Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes [J].
Bregent, Thibaud ;
Bouillon, Jean-Philippe ;
Poisson, Thomas .
ORGANIC LETTERS, 2020, 22 (19) :7688-7693
[3]  
Budzak S., 2022, CHEM-EUR J, V26, P28
[4]   Synthesis of Z-alkenes via visible light promoted photocatalytic E → Z isomerization under metal-free conditions [J].
Cai, Wenbin ;
Fan, Huaqiang ;
Ding, Dazhong ;
Zhang, Yongqiang ;
Wang, Wei .
CHEMICAL COMMUNICATIONS, 2017, 53 (96) :12918-12921
[5]   Unlocking Nicotinic Selectivity via Direct C-H Functionalization of (-)-Cytisine [J].
Campello, Hugo Rego ;
Del Villar, Silvia G. ;
Honraedt, Aurelien ;
Minguez, Teresa ;
Oliveira, A. Sofia F. ;
Ranaghan, Kara E. ;
Shoemark, Deborah K. ;
Bermudez, Isabel ;
Gotti, Cecilia ;
Sessions, Richard B. ;
Mulholland, Adrian J. ;
Wonnacott, Susan ;
Gallagher, Timothy .
CHEM, 2018, 4 (07) :1710-1725
[6]   Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines [J].
Chen, Xinzheng ;
Qiu, Shuxian ;
Wang, Sasa ;
Wang, Huifei ;
Zhai, Hongbin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (30) :6349-6352
[7]   Palladium-catalyzed selective oxidative olefination and arylation of 2-pyridones [J].
Chen, Yuye ;
Wang, Fen ;
Jia, Aiqun ;
Li, Xingwei .
CHEMICAL SCIENCE, 2012, 3 (11) :3231-3236
[8]   Visible-light-mediated minisci C-H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2as an oxidant [J].
Dong, Jianyang ;
Yue, Fuyang ;
Xu, Wentao ;
Song, Hongjian ;
Liu, Yuxiu ;
Wang, Qingmin .
GREEN CHEMISTRY, 2020, 22 (17) :5599-5604
[9]   Cancer Chemoprevention by Resveratrol: The p53 Tumor Suppressor Protein as a Promising Molecular Target [J].
Ferraz da Costa, Danielly C. ;
Fialho, Eliane ;
Silva, Jerson L. .
MOLECULES, 2017, 22 (06)
[10]   Palladium Acetate/[CPy][Br]: An Efficient Catalytic System towards the Synthesis of Biologically Relevant Stilbene Derivatives via Heck Cross-Coupling Reaction. [J].
Girase, Tejpalsingh Ramsingh ;
Patil, Kesharsingh J. ;
Kapdi, Anant R. ;
Gupta, Gaurav R. .
CHEMISTRYSELECT, 2020, 5 (14) :4251-4262