Copper-mediated synthesis of pyrazolo[1,5-a]-pyridines through oxidative linkage of C-C/N-N bonds

被引：28

作者：

Mohan, Darapaneni Chandra ^{[1
]}

Ravi, Chitrakar ^{[1
]}

Rao, Sadu Nageswara ^{[1
]}

Adimurthy, Subbarayappa ^{[1
]}

机构：

[1] CSIR Cent Salt & Marine Chem Res Inst, Acad Sci & Innovat Res, Bhavnagar 364002, Gujarat, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 12期

关键词：

AZAINDOLE DERIVATIVES; ACTIVATION SYNTHESIS; EFFICIENT SYNTHESIS; PYRROLE SYNTHESIS; CASCADE REACTION; CYCLIZATION; RECEPTOR; FUNCTIONALIZATION; HYDROAMINATION; HETEROCYCLES;

D O I：

10.1039/c5ob00018a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper-mediated synthesis of pyrazolo[1,5-a] pyridine-3-carboxylates through oxidative linkage of C-C and N-N bonds under mild reaction conditions is described. This protocol is applicable to a variety of pyridyl esters as well as various benzonitriles including nicotinonitrile, isonicotinonitrile and thiophene-2-carbonitrile. Better yields were observed with electron withdrawing substituted benzonitriles.

引用

页码：3556 / 3560

页数：5

共 55 条

[1] Aerobic Copper-Catalyzed Organic Reactions [J].

Allen, Scott E. ;

Walvoord, Ryan R. ;

Padilla-Salinas, Rosaura ;

Kozlowski, Marisa C. .

CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458

[2] Interactive SAR studies:: Rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists [J].

Bettinetti, L ;

Schlotter, K ;

Hübner, H ;

Gmeiner, P .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (21) :4594-4597

[3] Copper-mediated pyrazole synthesis from 2,3-allenoates or 2-alkynoates, amines and nitriles [J].

Chen, Bo ;

Zhu, Can ;

Tang, Yang ;

Ma, Shengming .

CHEMICAL COMMUNICATIONS, 2014, 50 (57) :7677-7679

[4] Silver triflate-copper(II) acetate cooperative catalysis in a cascade reaction for concise synthesis of 2-carbonyl H-pyrazolo[5,1-a]isoquinolines [J].

Chen, Zhiyuan ;

Gao, Liang ;

Ye, Shengqing ;

Ding, Qiuping ;

Wu, Jie .

CHEMICAL COMMUNICATIONS, 2012, 48 (33) :3975-3977

[5] Efficient Generation of Biologically Active H-Pyrazolo[5,1-a]isoquinolines via Multicomponent Reaction [J].

Chen, Zhiyuan ;

Wu, Jie .

ORGANIC LETTERS, 2010, 12 (21) :4856-4859

[6] Synthesis of functionalized H-pyrazolo[5,1-a]isoquinolines via sequential reactions of N′-(2-alkynylbenzylidene)hydrazides [J].

Chen, Zhiyuan ;

Su, Mingchao ;

Yu, Xingxin ;

Wu, Jie .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (22) :4641-4646

[7] Thermal and Microwave-Assisted Rapid Syntheses of Substituted Imidazo[1,2-a]pyridines Under Solvent- and Catalyst-Free Conditions [J].

Chunavala, Kaushik C. ;

Joshi, Girdhar ;

Suresh, Eringathodi ;

Adimurthy, Subbarayappa .

SYNTHESIS-STUTTGART, 2011, (04) :635-641

[8] Synthesis of two new heteroaromatic β-carboline-fused pentacycles.: Observation of a new intercalating agent [J].

Csányi, D ;

Hajós, G ;

Riedl, Z ;

Timári, G ;

Bajor, Z ;

Cochard, F ;

Sapi, J ;

Laronze, JY .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (15) :1767-1769

[9] Copper-catalyzed direct oxidative annulation of N-iminopyridinium ylides with terminal alkynes using O2 as oxidant [J].

Ding, Shengtao ;

Yan, Yuepeng ;

Jiao, Ning .

CHEMICAL COMMUNICATIONS, 2013, 49 (39) :4250-4252

[10] Copper-Catalyzed C-H Functionalization of Pyridines and Isoquinolines with Vinyl Azides: Synthesis of Imidazo Heterocycles [J].

Donthiri, Ramachandra Reddy ;

Pappula, Venkatanarayana ;

Reddy, N. Naresh Kumar ;

Bairagi, Dipayan ;

Adimurthy, Subbarayappa .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (22) :11277-11284

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