Multicomponent and One-pot Syntheses of Quinoxalines

被引:68
作者
Biesen, Lukas [1 ]
Mueller, Thomas J. J. [1 ]
机构
[1] Heinrich Heine Univ Dusseldorf, Inst Organ Chem & Makromol Chem, Univ Str 1, D-40225 Dusseldorf, Germany
关键词
Heterocycles; Multicomponent reactions; One-pot processes; Quinoxalines; TANDEM OXIDATION PROCESSES; STEREOSELECTIVE-SYNTHESIS; HETEROCYCLIC CHEMISTRY; 3-ETHYNYL QUINOXALINES; 3-COMPONENT SYNTHESIS; GREEN SYNTHESIS; SOLAR-CELLS; EFFICIENT; DERIVATIVES; NANOPARTICLES;
D O I
10.1002/adsc.202001219
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Quinoxalines represent bicyclic nitrogen-containing heterocycles with a wide array of applications. They exhibit a multitude of biological activities relevant in medicinal chemistry as well as a plethora of luminescence properties. Quinoxaline syntheses exploit the whole raft of multicomponent syntheses from domino to sequential or consecutive reactions, harvesting well-known synthetic concepts and reactions, such as Ugi-reactions, but also leading to the development of novel reactions and sequences. Diversity-oriented synthesis and transition metal catalyzed multicomponent reactions open efficient pathways to quinoxalines and quinoxaline-containing moieties in a one-pot fashion. This review outlines the underlying reaction-based principles of multicomponent syntheses of quinoxalines and summarizes recent developments quinoxaline-directed MCRs, illustrating their scopes.
引用
收藏
页码:980 / 1006
页数:27
相关论文
共 125 条
[1]   Luminescent materials incorporating pyrazine or quinoxaline moieties [J].
Achelle, Sylvain ;
Baudequin, Christine ;
Ple, Nelly .
DYES AND PIGMENTS, 2013, 98 (03) :575-600
[2]   Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine [J].
Ajani, Olayinka Oyewale .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 :688-715
[3]   Toxicity of Organic Fluorophores Used in Molecular Imaging: Literature Review [J].
Alford, Raphael ;
Simpson, Haley M. ;
Duberman, Josh ;
Hill, G. Craig ;
Ogawa, Mikako ;
Regino, Celeste ;
Kobayashi, Hisataka ;
Choyke, Peter L. .
MOLECULAR IMAGING, 2009, 8 (06) :341-354
[4]   IMPORTANCE OF HETEROCYCLIC CHEMISTRY: A REVIEW [J].
Arora, Pragi ;
Arora, Varun ;
Lamba, H. S. ;
Wadhwa, Deepak .
INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2012, 3 (09) :2947-2954
[5]  
Asif M.A., 2017, Int. J. Bioorg. Chem, V2, P146, DOI [DOI 10.11648/J.IJBC.20170203.20, 10.11648/j.ijbc.20170203.20]
[6]   A Robust Protocol for the Synthesis of Quinoxalines and 5H-Benzo[e][1,4]diazepines via the Acidless Ugi Reaction [J].
Ayaz, Muhammad ;
Martinez-Ariza, Guillermo ;
Hulme, Christopher .
SYNLETT, 2014, 25 (12) :1680-1684
[7]   Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction [J].
Ayaz, Muhammad ;
Xu, Zhigang ;
Hulme, Christopher .
TETRAHEDRON LETTERS, 2014, 55 (23) :3406-3409
[8]   A novel route to synthesize libraries of quinoxalines via Petasis methodology in two synthetic operations [J].
Ayaz, Muhammad ;
Dietrich, Justin ;
Hulme, Christopher .
TETRAHEDRON LETTERS, 2011, 52 (38) :4821-4823
[9]   A synthetic route to 11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline derivatives exploiting a three-component coupling strategy under microwave irradiation [J].
Azizian, J ;
Karimi, AR ;
Kazemizadeh, Z ;
Mohammadi, AA ;
Mohammadizadeh, MR .
TETRAHEDRON LETTERS, 2005, 46 (36) :6155-6157
[10]   Ugi-Based Approaches to Quinoxaline Libraries [J].
Azuaje, Jhonny ;
El Maatougui, Abdelaziz ;
Garcia-Mera, Xerardo ;
Sotelo, Eddy .
ACS COMBINATORIAL SCIENCE, 2014, 16 (08) :403-411