Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolinesY

被引：11

作者：

Sontakke, Geetanjali S. ^{[1
]}

Shukla, Rahul K. ^{[1
]}

Volla, Chandra M. R. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 17卷

关键词：

amination; heteroarylation; quinoline N-oxides; regioselective; triazoles; C-H FUNCTIONALIZATION; ONE-STEP CONVERSION; METAL-FREE; DIRECT ARYLATION; AZINE; ACTIVATION; MILD; SULFOXIMINATION; TRANSANNULATION; ALKYLATION;

D O I：

10.3762/bjoc.17.42

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of alpha-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.

引用

页码：485 / 493

页数：9

共 63 条

[1] Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines [J].

Aithagani, Sravan Kumar ;

Kumar, Mukesh ;

Yadav, Mahipal ;

Vishwakarma, Ram A. ;

Singh, Parvinder Pal .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (14) :5886-5894

[2] Regioselective Metal-Free Cross-Coupling of Quinoline N-Oxides with Boronic Acids [J].

Bering, Luis ;

Antonchick, Andrey P. .

ORGANIC LETTERS, 2015, 17 (12) :3134-3137

[3] Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].

Campeau, Louis-Charles ;

Stuart, David R. ;

Leclerc, Jean-Philippe ;

Bertrand-Laperle, Megan ;

Villemure, Elisia ;

Sun, Ho-Yan ;

Lasserre, Sandrine ;

Guimond, Nicolas ;

Lecavallier, Melanie ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306

[4] Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems [J].

Chattopadhyay, Buddhadeb ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :862-872

[5] Base-Promoted Cross-Dehydrogenative Coupling of Quinoline N-Oxides with 1,3-Azoles [J].

Chen, Xiaopei ;

Cui, Xiuling ;

Yang, Fangfang ;

Wu, Yangjie .

ORGANIC LETTERS, 2015, 17 (06) :1445-1448

[6] TsOH•H2O-mediated N-amidation of quinoline N-oxides: facile and regioselective synthesis of N-(quinolin-2-yl)amides [J].

Chen, Xinghua ;

Peng, Mei ;

Huang, Hao ;

Zheng, Yangfan ;

Tao, Xiaojun ;

He, Chunlian ;

Xiao, Yi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (34) :6202-6205

[7] Direct 2-acetoxylation of quinoline N-oxides via copper catalyzed C-H bond activation [J].

Chen, Xuan ;

Zhu, Chongwei ;

Cui, Xiuling ;

Wu, Yangjie .

CHEMICAL COMMUNICATIONS, 2013, 49 (61) :6900-6902

[8] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].

Cho, Seung Hwan ;

Hwang, Seung Jun ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+

[9] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

[10] A virtual screening approach to finding novel and potent antagonists at the melanin-concentrating hormone 1 receptor [J].

Clark, DE ;

Higgs, C ;

Wren, SP ;

Dyke, HJ ;

Wong, M ;

Norman, D ;

Lockey, PM ;

Roach, AG .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (16) :3962-3971

← 1 2 3 4 5 6 7 →