Copper-mediated three-component synthesis of 3-cyanoimidazo[1,2-a]pyridines

被引：49

作者：

Wen, Qiaodong ^{[1
]}

Lu, Ping ^{[1
]}

Wang, Yanguang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 84期

关键词：

INTRAMOLECULAR PROTON-TRANSFER; ONE-POT SYNTHESIS; BETA-KETO-ESTERS; MULTICOMPONENT REACTION; ANTIVIRAL ACTIVITY; DIRECT ACCESS; 2-AMINOPYRIDINES; IMIDAZOPYRIDINES; CYCLIZATION; CYANATION;

D O I：

10.1039/c5cc05821j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A copper-mediated three-component approach towards the synthesis of 3-cyanoimidazo[1,2-a]pyridines from 2-aminopyridines, aceto-phenones and benzyl cyanide was developed. This cascade reaction proceeds through a copper-mediated oxidative release of cyanide from benzyl cyanide, a copper-mediated Ortoleva-King reaction, and a copper-catalyzed cyanation.

引用

页码：15378 / 15381

页数：4

共 60 条

[21] Synthesis of imidazo[1,2-a]pyridines as antiviral agents [J].

Gueiffier, A ;

Mavel, S ;

Lhassani, M ;

Elhakmaoui, A ;

Snoeck, R ;

Andrei, G ;

Chavignon, O ;

Teulade, JC ;

Witvrouw, M ;

Balzarini, J ;

De Clercq, E ;

Chapat, JP .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (25) :5108-5112

[22] Structural Requirements for Eszopiclone and Zolpidem Binding to the γ-Aminobutyric Acid Type-A (GABAA) Receptor Are Different [J].

Hanson, Susan M. ;

Morlock, Elaine V. ;

Satyshur, Kenneth A. ;

Czajkowski, Cynthia .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (22) :7243-7252

[23] Heteroaromatic imidazo[1,2-a]pyridines synthesis from C-H/N-H oxidative cross-coupling/cyclization [J].

He, Chuan ;

Hao, Jing ;

Xu, Huan ;

Mo, Yiping ;

Liu, Huiying ;

Han, Juanjuan ;

Lei, Aiwen .

CHEMICAL COMMUNICATIONS, 2012, 48 (90) :11073-11075

[24] Conversion of Pyridine to Imidazo[1,2-a]pyridines by Copper-Catalyzed Aerobic Dehydrogenative Cyclization with Oxime Esters [J].

Huang, Huawen ;

Ji, Xiaochen ;

Tang, Xiaodong ;

Zhang, Min ;

Li, Xianwei ;

Jiang, Huanfeng .

ORGANIC LETTERS, 2013, 15 (24) :6254-6257

[25] Ligand-based structural hypotheses for virtual screening [J].

Jain, AN .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (04) :947-961

[26] Copper-catalyzed cyanation of arenes using benzyl nitrile as a cyanide anion surrogate [J].

Jin, Jisong ;

Wen, Qiaodong ;

Lu, Ping ;

Wang, Yanguang .

CHEMICAL COMMUNICATIONS, 2012, 48 (79) :9933-9935

[27] Lead Optimization of a Novel Series of Imidazo[1,2-a]pyridine Amides Leading to a Clinical Candidate (Q203) as a Multi- and Extensively-Drug-Resistant Anti-tuberculosis Agent [J].

Kang, Sunhee ;

Kim, Ryang Yeo ;

Seo, Min Jung ;

Lee, Saeyeon ;

Kim, Young Mi ;

Seo, Mooyoung ;

Seo, Jeong Jea ;

Ko, Yoonae ;

Choi, Inhee ;

Jang, Jichan ;

Nam, Jiyoun ;

Park, Seijin ;

Kang, Hwankyu ;

Kim, Hyung Jun ;

Kim, Jungjun ;

Ahn, Sujin ;

Pethe, Kevin ;

Nam, Kiyean ;

No, Zaesung ;

Kim, Jaeseung .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (12) :5293-5305

[28] Synthesis of Aromatic Nitriles Using Nonmetallic Cyano-Group Sources [J].

Kim, Jinho ;

Kim, Hyun Jin ;

Chang, Sukbok .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) :11948-11959

[29] Copper-Mediated Sequential Cyanation of Aryl C-B and Arene C-H Bonds Using Ammonium Iodide and DMF [J].

Kim, Jinho ;

Choi, Jiho ;

Shin, Kwangmin ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) :2528-2531

[30] The reaction of iodine with some ketones in the presence of pyridine [J].

King, LC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :894-895

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