Photocatalyst-free decarboxylative aminoalkylation of imidazo[1,2-a]pyridines with N-aryl glycines enabled by visible light

被引:41
作者
Ji, Jiu-Jian [1 ]
Zhu, Zhi-Qiang [1 ,2 ]
Xiao, Li-Jin [1 ]
Guo, Dong [1 ]
Zhu, Xiao [1 ]
Tang, Juan [3 ]
Wu, Jun [1 ]
Xie, Zong-Bo [1 ]
Le, Zhang-Gao [1 ,2 ]
机构
[1] East China Univ Technol, Sch Chem Biol & Mat Sci, Nanchang 330013, Jiangxi, Peoples R China
[2] East China Univ Technol, State Key Lab Nucl Resources & Environm, Nanchang 330013, Jiangxi, Peoples R China
[3] Jiangxi Normal Univ, Minist Educ, Key Lab Funct Small Organ Mol, Dept Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 21期
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
DEHYDROGENATIVE-COUPLING REACTION; ALPHA-AMINO-ACIDS; ONE-POT SYNTHESIS; PHOTOREDOX CATALYSIS; MOLECULAR-OXYGEN; IN-VITRO; DERIVATIVES; INHIBITORS; IMIDAZOHETEROCYCLES; FUNCTIONALIZATION;
D O I
10.1039/c9qo00935c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, green and efficient visible-light-promoted decarboxylative aminoalkylation reaction of imidazo[1,2-a]pyridines with N-aryl glycines has been described. A diverse range of imidazo[1,2-a]pyridines undergoes the reaction well with N-aryl glycines to afford the desired corresponding products in good to high yields. This photocatalyst-free decarboxylative protocol not only manifests high regio-selectivity to biologically important imidazo[1,2-a]pyridines, but also avoids the use of expensive photosensitizers and extra additives, which makes this decarboxylative coupling more practical and sustainable.
引用
收藏
页码:3693 / 3697
页数:5
相关论文
共 67 条
[1]   Design, synthesis and in vitro antimicrobial evaluation of novel Imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole motifs [J].
Al-Tel, Taleb H. ;
Al-Qawasmeh, Raed A. ;
Zaarour, Rania .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (05) :1874-1881
[2]   DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY [J].
ALMIRANTE, L ;
POLO, L ;
MUGNAINI, A ;
PROVINCIALI, E ;
RUGARLI, P ;
BIANCOTTI, A ;
GAMBA, A ;
MURMANN, W .
JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) :305-+
[3]   Synthesis of imidazo[1,2-a]pyridines: a decade update [J].
Bagdi, Avik Kumar ;
Santra, Sougata ;
Monir, Kamarul ;
Hajra, Alakananda .
CHEMICAL COMMUNICATIONS, 2015, 51 (09) :1555-1575
[4]  
Bloom S, 2018, NAT CHEM, V10, P205, DOI [10.1038/nchem.2888, 10.1038/NCHEM.2888]
[5]   The cellular phenotype of AZ703, a novel selective imidazo[1,2-a]pyridine cyclin-dependent kinase inhibitor [J].
Byth, KF ;
Geh, C ;
Forder, CL ;
Oakes, SE ;
Thomas, AP .
MOLECULAR CANCER THERAPEUTICS, 2006, 5 (03) :655-664
[6]   AZ703, an imidazo[1,2-a]pyridine inhibitor of cyclin-dependent kinases 1 and 2, induces E2F-1-dependent apoptosis enhanced by depletion of cyclin-dependent kinase 9 [J].
Cai, DP ;
Byth, KF ;
Shapiro, GI .
CANCER RESEARCH, 2006, 66 (01) :435-444
[7]   Amphiphilic methyleneamino synthon through organic dye catalyzed-decarboxylative aminoalkylation [J].
Chen, Li ;
Chao, Chin Sheng ;
Pan, Yuanhang ;
Dong, Sheng ;
Teo, Yew Chin ;
Wang, Jian ;
Tan, Choon-Hong .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (35) :5922-5925
[8]   General and Efficient Copper-Catalyzed Three-Component Coupling Reaction towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem [J].
Chernyak, Natalia ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (15) :2743-2746
[9]   Recent progress in the pharmacology of imidazo[1,2-a]pyridines [J].
Enguehard-Gueiffier, Cecile ;
Gueiffier, Alain .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (09) :888-899
[10]   Colorless, Transparent, Dye-Doped Polymer Films Exhibiting Tunable Luminescence Color: Controlling the Dual-Color Luminescence of 2-(2′-Hydroxyphenyl)imidazo[1,2-a]pyridine Derivatives with the Surrounding Matrix [J].
Furukawa, Shintaro ;
Shono, Hideaki ;
Mutai, Toshiki ;
Araki, Koji .
ACS APPLIED MATERIALS & INTERFACES, 2014, 6 (18) :16065-16070