Hypervalent Iodine(III) Promoted Direct Synthesis of Imidazo[1,2-a]pyrimidines

被引:65
作者
Qian, Guangyin [1 ]
Liu, Bingxin [1 ]
Tan, Qitao [1 ]
Zhang, Siwen [1 ]
Xu, Bin [1 ,2 ,3 ]
机构
[1] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Dept Chem, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
Synthetic methods; Nitrogen heterocycles; C-H functionalization; Amination; Iodine; N BOND FORMATION; C-H AMINATION; OXIDATIVE CYCLIZATION; EFFICIENT ACCESS; DERIVATIVES; ALKENES; ARENES; CYCLOAMINATION; INHIBITORS; REACTIVITY;
D O I
10.1002/ejoc.201402456
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and mild synthesis of imidazo[1,2-a]pyrimidine derivatives has been developed from readily available pyrimidyl arylamines or enamines through a hypervalent iodine-promoted intramolecular C-H bond cycloamination reaction. This protocol allows for the facile construction of biologically active bicyclic imidazo[1,2-alpha]pyrimidine skeletons as well as other imidazo[1,2-alpha]-type fused heterocycles.
引用
收藏
页码:4837 / 4843
页数:7
相关论文
共 86 条
[81]   Palladium-Assisted Regioselective C-H Cyanation of Heteroarenes Using Isonitrile as Cyanide Source [J].
Xu, Shuguang ;
Huang, Xiaomei ;
Hong, Xiaohu ;
Xu, Bin .
ORGANIC LETTERS, 2012, 14 (17) :4614-4617
[82]   Synthesis and characterization of new trifluoromethyl substituted 3-ethoxycarbonyl- and 3-pyrimidin-2-yl)-(1,2,3)-oxathiazinane-S-oxides [J].
Zanatta, Nilo ;
Borchhardt, Deise M. ;
Flores, Darlene C. ;
Coelho, Helena S. ;
Marchi, Tiago M. ;
Flores, Alex F. C. ;
Bonacorso, Helio G. ;
Martins, Marcos A. P. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (02) :335-341
[83]   Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission [J].
Zhao, Dongbing ;
Hu, Junyi ;
Wu, Ningjie ;
Huang, Xiaolei ;
Qin, Xurong ;
Lan, Jingbo ;
You, Jingsong .
ORGANIC LETTERS, 2011, 13 (24) :6516-6519
[84]  
Zhdankin V. V., 2014, Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Application of Polyvalent Iodine Compounds
[85]   Direct synthesis of ortho-dihalogenated arylpyrimidines using calcium halides as halogen sources [J].
Zheng, Xiaojian ;
Song, Bingrui ;
Li, Guifei ;
Liu, Bingxin ;
Deng, Hongmei ;
Xu, Bin .
TETRAHEDRON LETTERS, 2010, 51 (50) :6641-6645
[86]   Palladium-Catalyzed Regioselective C-H Bond ortho-Acetoxylation of Arylpyrimidines [J].
Zheng, Xiaojian ;
Song, Bingrui ;
Xu, Bin .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) :4376-4380