Trifluoroacetic Acid Mediated One-Pot Synthesis of Furo-Fused Quinoxalines/Pyrazines

被引：18
作者：
Saini, Kapil Mohan [1 ]
Kumar, Sonu [1 ]
Patel, Monika [1 ]
Saunthwal, Rakesh K. [1 ]
Verma, Akhilesh K. [1 ]
机构：
[1] Univ Delhi, Dept Chem, Delhi 110007, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 25期
关键词：
Nitrogen heterocycles; Cyclization; Cross-coupling; Alkynes; Oxygen heterocycles; Fused-ring systems; CATALYZED DOMINO REACTIONS; C-H ACTIVATION; ELECTROPHILIC CYCLIZATION; BIOLOGICAL-ACTIVITY; CASCADE REACTION; PALLADIUM; ALKYNES; HETEROCYCLES; STRATEGY; ANALOGS;
D O I：
10.1002/ejoc.201700541
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A trifluoroacetic acid promoted step-economical one-pot approach to the synthesis of furo-fused quinoxalines/pyrazines by the reaction of 2,3-dichloroquinoxalines/pyrazines with alkynes is described. The reaction involves a selective insitu Sonogashira coupling step and a hydroxylation followed by a metal-free 5-endo-dig cyclization. Preliminary experiments show that trifluoroacetic acid acts as a source of oxygen for the oxyarylation step, and isotopic labeling studies support the proposal that the mechanistic pathway involves activation of the alkyne by the acidic medium. Various kinds of substituents are tolerated, which should prove valuable for structural and biological investigations.
引用
收藏
页码：3707 / 3715
页数：9
相关论文
共 50 条
[41]   DMAP-catalyzed cascade reaction: one-pot synthesis of benzofurans in water [J].
Shang, Yongjia ;
Wang, Cuie ;
He, Xinwei ;
Ju, Kai ;
Zhang, Min ;
Yu, Shuyan ;
Wu, Jiaping .
TETRAHEDRON, 2010, 66 (50) :9629-9633
[42]   One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds [J].
Song, Qiao ;
Liu, Yan ;
Cai, Linlin ;
Cao, Xinyu ;
Qian, Shan ;
Wang, Zhouyu .
CHINESE CHEMICAL LETTERS, 2021, 32 (05) :1713-1716
[43]   Lewis Acid Mediated One-Pot Synthesis of Aryl/Heteroaryl-Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence [J].
Sureshbabu, Radhakrishnan ;
Saravanan, Velu ;
Dhayalan, Vasudevan ;
Mohanakrishnan, Arasambattu K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) :922-935
[44]   One-Pot Multicomponent Synthesis of Azaindoles and Pyrroles from One Molecule of a Silicon-Tethered Diyne and Three or Two Molecules of Organonitriles Mediated by Zirconocene [J].
Zhang, Shaoguang ;
Sun, Xiaohua ;
Zhang, Wen-Xiong ;
Xi, Zhenfeng .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) :12608-12617
[45]   Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines [J].
Niesobski, Patrik ;
Martinez, Ivette Santana ;
Kustosz, Sebastian ;
Mueller, Thomas J. J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) :5214-5218
[46]   Bronsted Acid-Mediated Domino One-Pot Dual C-C Bond Formation: Chemoselective Synthesis of Fused Tricyclic Ketones [J].
Niharika, Pedireddi ;
Ramulu, Bokka Venkat ;
Satyanarayana, Gedu .
ACS OMEGA, 2018, 3 (01) :218-228
[47]   Hypervalent-iodine mediated one-pot synthesis of isoxazolines and isoxazoles bearing a difluoromethyl phosphonate moiety [J].
Pajkert, Romana ;
Koroniak, Henryk ;
Kafarski, Pawel ;
Roeschenthaler, Gerd-Volker .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (22) :4871-4876
[48]   Phosphite-Mediated Synthesis of Benzimidazoles: A One-Pot Four-Component Approach from Nitrophenols [J].
El Kaiem, Laurent ;
Grimaud, Laurence ;
Purumandla, Srinivas Reddy .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (31) :6177-6180
[49]   A Versatile Iron-Catalyzed Protocol for the One-Pot Synthesis of Isoxazoles or Isoxazolines from the Same Propargylic Alcohols [J].
Debleds, Olivier ;
Gayon, Eric ;
Ostaszuk, Emilie ;
Vrancken, Emmanuel ;
Campagne, Jean-Marc .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (40) :12207-12213
[50]   [Pd]-Catalyzed Intermolecular Coupling and Acid Mediated Intramolecular Cyclodehydration: One-Pot Synthesis of Indenes [J].
Niharika, Pedireddi ;
Satyanarayana, Gedu .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (08) :971-979
12345