Palladium/copper-catalyzed tandem Sonogashira coupling/lactonization of methyl 2-(2',2'-dibromovinyl)benzoate with terminal alkynes: Facile access to 3-alkynyl isocoumarins

被引:5
作者
Liu, Xiaozu [1 ]
Chen, Guojun [1 ]
Zhou, Yuxiang [1 ]
Liu, Peijun [1 ]
机构
[1] Zunyi Med Univ, Pharm Sch, Zunyi 563006, Peoples R China
基金
中国国家自然科学基金;
关键词
PdCl2; Tandem reaction; Sonogashira coupling; Lactonization; 3-Alkynyl isocoumarins; 3-SUBSTITUTED ISOCOUMARINS; FUNCTIONALIZED ISOCOUMARINS; INTRAMOLECULAR CYCLIZATION; BENZOIC-ACIDS; DERIVATIVES; EFFICIENT; ANALOGS; 2-(GEM-DIBROMOVINYL)PHENOLS(THIOPHENOLS); GYMNOPALYNES; ANTIBIOTICS;
D O I
10.1016/j.tetlet.2018.07.017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient palladium/copper-catalyzed tandem Sonogashira reaction/lactonization of methyl 2-(2',2'-dibromovinyl)benzoate with terminal alkynes has been developed. This facile and direct approach furnishes a variety of 3-alkynyl isocoumarins in moderate to good yields under mild reaction conditions. Furthermore, this method enables concise total synthesis of natural products 3'-hydroxycorfin and gymnopalynes A (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3151 / 3154
页数:4
相关论文
共 34 条
[1]   Metal-catalyzed synthesis of isocoumarin derivatives (microreview) [J].
Ashraf, Zaman .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (03) :149-151
[2]   Cascade Palladium- and Copper-Catalysed Aromatic Heterocycle Synthesis: The Emergence of General Precursors [J].
Ball, Catherine J. ;
Willis, Michael C. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (03) :425-441
[3]   Copper/Palladium-Catalyzed Cyclization/Cross-Coupling Cascade Reaction of 2-gem-Dibromovinyl Aryl Selenides: Synthesis of 2-Substituted Benzo[b]selenophenes [J].
Bilheri, Filipe N. ;
Pistoia, Renan P. ;
Back, Davi F. ;
Zeni, Gilson .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (23) :4208-4216
[4]   Rubromycins:: Structurally intriguing, biologically valuable, synthetically challenging antitumour antibiotics [J].
Brasholz, Malte ;
Soergel, Sebastian ;
Azap, Cengiz ;
Reissig, Hans-Ulrich .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (23) :3801-3814
[5]   A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights into gem-Dibromoolefin Reactivity [J].
Bryan, Christopher S. ;
Lautens, Mark .
ORGANIC LETTERS, 2010, 12 (12) :2754-2757
[6]   Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins [J].
Casnati, Alessandra ;
Maggi, Raimondo ;
Maestri, Giovanni ;
Della Ca, Nicola ;
Motti, Elena .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (15) :8296-8303
[7]   An efficient tandem elimination-cyclization-desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates [J].
Chen, Wei ;
Li, Pinhua ;
Miao, Tao ;
Meng, Ling-Guo ;
Wang, Lei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (03) :420-424
[8]   Efficient and convenient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling in the preparation of corfin analogues [J].
Dasaradhan, Changalaraya ;
Kumar, Yadavalli Suneel ;
Prabakaran, Kamalakannan ;
Khan, Faziur-Rahman Nawaz ;
Jeong, Euh Duck ;
Chung, Eun Hyuk .
TETRAHEDRON LETTERS, 2015, 56 (06) :784-788
[9]   Efficient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling in the preparation of 3′-hydroxycorfin and gymnopalynes A analogues [J].
Dasaradhan, Changalaraya ;
Kumar, Yadavalli Suneel ;
Khan, Fazlur-Rahman Nawaz ;
Jeong, Euh Duck ;
Chung, Eun Hyuk .
TETRAHEDRON LETTERS, 2015, 56 (01) :187-191
[10]  
Diederich F, 2005, ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE, pV