An efficient iodine-DMSO catalyzed synthesis of quinoxaline derivatives

被引:37
作者
Xie, Caixia [1 ]
Zhang, Zeyuan [1 ]
Yang, Bingchuan [1 ]
Song, Gaolei [1 ]
Gao, He [1 ]
Wen, Leilin [1 ]
Ma, Chen [1 ,2 ,3 ]
机构
[1] Shandong Univ, Sch Chem & Chem Engn, Key Lab Special Funct Aggregated Mat, Minist Educ, Jinan 250100, Peoples R China
[2] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
[3] Peking Union Med Coll, Beijing 100050, Peoples R China
基金
美国国家科学基金会;
关键词
Quinoxaline; One-pot synthesis; Iodine/DMSO; Broad range of substrates; ONE-POT SYNTHESIS; OXIDATIVE SYSTEM; METHYL KETONES; TANDEM PROCESS; CONSTRUCTION; CYCLIZATION; STRATEGY; OXIDANT; DESIGN; ACID;
D O I
10.1016/j.tet.2015.02.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient iodine-DMSO catalyzed system for the synthesis of quinoxaline derivatives was developed. The construction of this quinoxaline system went through a one-pot oxidation/cyclization process. The reaction afforded a variety of products in good to excellent yields. This methodology has potential applications in the synthesis of biologically and medicinally relevant compounds. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1831 / 1837
页数:7
相关论文
共 48 条
[1]   Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization [J].
Ashikari, Yosuke ;
Shimizu, Akihiro ;
Nokami, Toshiki ;
Yoshida, Jun-ichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16070-16073
[2]   Efficient synthesis of quinoxalines with hypervalent iodine as a catalyst [J].
Chen, Chung-Yu ;
Hu, Wan-Ping ;
Liu, Mei-Chun ;
Yan, Pi-Cheng ;
Wang, Jeh-Jeng ;
Chung, Mei-Ing .
TETRAHEDRON, 2013, 69 (46) :9735-9741
[3]   A new ruthenium-catalyzed approach for quinoxalines from o-phenylenediamines and vicinal-diols [J].
Cho, Chan Sik ;
Oh, Sung Gi .
TETRAHEDRON LETTERS, 2006, 47 (32) :5633-5636
[4]   Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts [J].
Climent, M. J. ;
Corma, A. ;
Hernandez, J. C. ;
Hungria, A. B. ;
Iborra, S. ;
Martinez-Silvestre, S. .
JOURNAL OF CATALYSIS, 2012, 292 :118-129
[5]  
Dailey S, 2001, J MATER CHEM, V11, P2238, DOI 10.1039/b104674h
[6]   An efficient and convenient protocol for the synthesis of quinoxalines and dihydropyrazines via cyclization-oxidation processes using HClO4•SiO2 as a heterogeneous recyclable catalyst [J].
Das, Biswanath ;
Venkateswarlu, Katta ;
Suneel, Kanaparthy ;
Majhi, Anjoy .
TETRAHEDRON LETTERS, 2007, 48 (31) :5371-5374
[7]   SYNTHESIS AND ANTI-BACTERIAL ACTIVITY OF SOME 3-[(ALKYLTHIO)METHYL]QUINOXALINE 1-OXIDE DERIVATIVES [J].
DIRLAM, JP ;
PRESSLITZ, JE ;
WILLIAMS, BJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (08) :1122-1126
[8]   A one-pot synthetic strategy for construction of the dibenzodiazepine skeleton via a transition metal-free process [J].
Fang, Shuai ;
Niu, Xiaoyi ;
Zhang, Zeyuan ;
Sun, Yan ;
Si, Xiaomeng ;
Shan, Cuicui ;
Wei, Lei ;
Xu, Aiqing ;
Feng, Lei ;
Ma, Chen .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (35) :6895-6900
[9]   One-Pot Synthesis of Benzo[4,5]imidazo[1,2-a]quinazoline Derivatives via Facile Transition-Metal-Free Tandem Process [J].
Fang, Shuai ;
Niu, Xiaoyi ;
Yang, Bingchuan ;
Li, Yanqiu ;
Si, Xiaomeng ;
Feng, Lei ;
Ma, Chen .
ACS COMBINATORIAL SCIENCE, 2014, 16 (07) :328-332
[10]   I2-Promoted Selective Oxidative Cross-Coupling/Annulation of 2-Naphthols with Methyl Ketones: A Strategy To Build Naphtho[2,1-b]furan-1(2H)-ones with a Quaternary Center [J].
Gao, Qinghe ;
Wu, Xia ;
Liu, Shan ;
Wu, Anxin .
ORGANIC LETTERS, 2014, 16 (06) :1732-1735