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
[41]   Synthesis of some new 4-styryltetrazolo[1,5-a]quinoxaline and 1-substituted-4-styryl[1,2,4]triazolo[4,3-a]quinoxaline derivatives as potent anticonvulsants [J].
Wagle, Shivananda ;
Adhikari, Airody Vasudeva ;
Kumari, Nalilu Suchetha .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (03) :1135-1143
[42]   Copper-Catalyzed Synthesis of Quinoxalines with o-Phenylenediamine and Terminal Alkyne in the Presence of Bases [J].
Wang, Wen ;
Shen, Yongwen ;
Meng, Xu ;
Zhao, Mingming ;
Chen, Yongxin ;
Chen, Baohua .
ORGANIC LETTERS, 2011, 13 (17) :4514-4517
[43]   Coupling of Methyl Ketones and Primary or Secondary Amines Leading to α-Ketoamides [J].
Wei, Wei ;
Shao, Ying ;
Hu, Huayou ;
Zhang, Feng ;
Zhang, Chao ;
Xu, Yuan ;
Wan, Xiaobing .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7157-7165
[44]   Switching Regioselectivity of β-Ketothioamides by Means of Iodine Catalysis: Synthesis of Thiazolylidenes and 1,4-Dithiines [J].
Wen, Li-Rong ;
Men, Lian-Bin ;
He, Tao ;
Ji, Guo-Jing ;
Li, Ming .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (17) :5028-5033
[45]   New routes for the synthesis of fused pyrrole scaffolds through transition metal-free tandem reactions [J].
Yang, Bingchuan ;
Huang, Zixiao ;
Guan, Hegen ;
Niu, Xiaoyi ;
Li, Yanqiu ;
Fang, Shuai ;
Ma, Chen .
TETRAHEDRON LETTERS, 2013, 54 (45) :5994-5997
[46]   A novel kind of dimmer (excimer)-induced-AIE compound 2-phenylisothiazolo[5,4-b]pyridin-3(2H)-one as high selective bisulfite anion probe [J].
Yang, Bingchuan ;
Niu, Xiaoyi ;
Huang, Zixiao ;
Zhao, Cuihua ;
Liu, Yang ;
Ma, Chen .
TETRAHEDRON, 2013, 69 (38) :8250-8254
[47]   One-Pot Synthesis of Benzo[1,4]thiazin-3(4H)-ones and a Theoretical Study of the S-N Type Smiles Rearrangement Mechanism [J].
Zhao, Yongmei ;
Wu, Yanmiao ;
Jia, Jiong ;
Zhang, Dongju ;
Ma, Chen .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) :8501-8506
[48]   Direct One-Pot Synthesis of Luotonin F and Analogues via Rational Logical Design [J].
Zhu, Yan-ping ;
Fei, Zhuan ;
Liu, Mei-cai ;
Jia, Feng-cheng ;
Wu, An-xin .
ORGANIC LETTERS, 2013, 15 (02) :378-381