Intermolecular cyclization of N-methylanilines and maleimides to tetrahydroquinolines via K2S2O8 promoted C(sp3)-H activation

被引:27
作者
Yadav, Arvind K. [1 ]
Yadav, Lai Dhar S. [1 ]
机构
[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India
关键词
Cyclization; N-Methylanilines; Maleimides; Heterocycles; Radical reactions; Tetrahydroquinolines; H BOND ACTIVATION; ARYLBORONIC ACIDS; AEROBIC OXYSULFONYLATION; CATALYZED ARYLATION; COUPLING REACTIONS; TERTIARY ANILINES; COPPER; FUNCTIONALIZATION; DERIVATIVES; PALLADIUM;
D O I
10.1016/j.tetlet.2016.02.078
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free, novel and convenient way for the direct cyclization of N-methylanilines with maleimides to tetrahydroquinolines via C(sp(3))-H activation is reported. The protocol utilizes inexpensive and easy to handle K2S2O8 as a radical surrogate and involves sequential formation of C(sp(3))-C(sp(2)) and C(sp(2))-C(sp(2)) bonds in a one-pot procedure at room temperature. The method affords excellent yield of tricyclic compounds incorporating biologically important tetrahydroquinoline core. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1489 / 1491
页数:3
相关论文
共 55 条
[1]   Thioesterification of Alkylbenzenes with Thiols via Copper-Catalyzed Cross-Dehydrogenative Coupling without a Directing Group [J].
Ali, Wajid ;
Guin, Srimanta ;
Rout, Saroj Kumar ;
Gogoi, Anupal ;
Patel, Bhisma K. .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) :3099-3105
[2]  
Banerjee S, 2010, PHARM LETT, V2, P154
[3]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[4]   Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].
Campbell, Alison N. ;
Stahl, Shannon S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863
[5]   K2S2O8-Mediated Aerobic Oxysulfonylation of Olefins into β-Keto Sulfones in Aqueous Media [J].
Chawla, Ruchi ;
Singh, Atul K. ;
Yadav, Lal Dhar S. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (10) :2032-2036
[6]   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
[7]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[8]   A one-pot strategy to synthesize β-ketophosphonates: silver/copper catalyzed direct oxyphosphorylation of alkynes with H-phosphonates and oxygen in the air [J].
Chen, Xin ;
Li, Xu ;
Chen, Xiao-Lan ;
Qu, Ling-Bo ;
Chen, Jian-Yu ;
Sun, Kai ;
Liu, Zhi-Dong ;
Bi, Wen-Zhu ;
Xia, Ying-Ya ;
Wu, Hai-Tao ;
Zhao, Yu-Fen .
CHEMICAL COMMUNICATIONS, 2015, 51 (18) :3846-3849
[9]   Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines:: A versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones [J].
Cheng, D ;
Zhou, JL ;
Saiah, E ;
Beaton, G .
ORGANIC LETTERS, 2002, 4 (25) :4411-4414
[10]   Metal-free oxidative direct C(sp3)-H bond functionalization of ethers with α,α-diaryl allylic alcohols [J].
Chu, Xue-Qiang ;
Meng, Hua ;
Zi, You ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
CHEMICAL COMMUNICATIONS, 2014, 50 (68) :9718-9721