Cu-Catalyzed Radical Cascade Annulations of Alkyne-Tethered N-Alkoxyamides with Air: Facile Access to Isoxazolidine/1,2-Oxazinane-Fused Isoquinolin-1(2H)-ones

被引:51
作者
Chen, Fei [1 ]
Lai, Sheng-Qiang [1 ]
Zhu, Fei-Fei [1 ]
Meng, Qiang [1 ]
Jiang, Yu [1 ]
Yu, Wei [1 ]
Han, Bing [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
copper/air catalytic system; cascade annulation; isoquinolin-1(2H)-one; isoxazolidine; 1,2-oxazinane; RHODIUM(III)-CATALYZED INTRAMOLECULAR ANNULATION; H BOND FUNCTIONALIZATION; ELECTROCHEMICAL SYNTHESIS; OXIDATIVE CYCLOADDITION; ISOQUINOLONE SYNTHESIS; EFFICIENT SYNTHESIS; MOLECULAR-OXYGEN; ACTIVATION; ALKENES; CYCLIZATION;
D O I
10.1021/acscatal.8b02445
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A series of structurally important isoxazolidine/1,2-oxazinane-fused isoquinolin-1(2H)-ones have been facilely synthesized via efficient Cu-catalyzed aerobic oxidative radical cascade annulations of alkyne-tethered N-alkoxyamides. This method features air as the environment-friendly oxidant and has the merits of a cheap catalyst, broad substrates scope, high atom economy, and simple operation.
引用
收藏
页码:8925 / 8931
页数:13
相关论文
共 103 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]   Synthesis and evaluation of novel 4-[(3H,3aH,6aH)-3-phenyl)-4,6-dioxo-2-phenyldihydro-2H-pyrrolo[3,4-d] isoxazol-5(3H,6H,6aH)-yl]benzoic acid derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents [J].
Anand, Preet ;
Singh, Baldev .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (01) :521-530
[3]   Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry [J].
Berthet, Matheo ;
Cheviett, Thomas ;
Dujardin, Gilles ;
Parrot, Isabelle ;
Martinez, Jean .
CHEMICAL REVIEWS, 2016, 116 (24) :15235-15283
[4]   Iterative, aqueous synthesis of β3-oligopeptides without coupling reagents [J].
Carrillo, N ;
Davalos, EA ;
Russak, JA ;
Bode, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1452-1453
[5]   Total synthesis of (+)-phyllantidine [J].
Carson, Cheryl A. ;
Kerr, Michael A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6560-6563
[6]   Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines [J].
Chakrabarty, Shyamal ;
Chatterjee, Indranil ;
Wibbeling, Birgit ;
Daniliuc, Constantin Gabriel ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (23) :5964-5968
[7]   Formation of Isoxazolidines by Enantioselective Copper-Catalyzed Annulation of 2-Nitrosopyridine with Allylstannanes [J].
Chatterjee, Indranil ;
Froehlich, Roland ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11257-11260
[8]   Cp*Co(III)-Catalyzed C-H Functionalization Cascade of N-Methoxyamides with Alkynedione for the Synthesis of Indolizidines [J].
Chavan, Lahu N. ;
Gollapelli, Krishna Kumar ;
Chegondi, Rambabu ;
Pawar, Amit B. .
ORGANIC LETTERS, 2017, 19 (08) :2186-2189
[9]   Visible light photoredox-controlled reactions of N-radicals and radical ions [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056
[10]   Visible light-driven photocatalytic generation of sulfonamidyl radicals for alkene hydroamination of unsaturated sulfonamides [J].
Chen, Jun ;
Guo, Hong-Mei ;
Zhao, Quan-Qing ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
CHEMICAL COMMUNICATIONS, 2018, 54 (50) :6780-6783