Copper-catalyzed C(sp3)-H functionalization of ketones with vinyl azides: synthesis of substituted-1H-pyrroles

被引:32
作者
Donthiri, Ramachandra Reddy [1 ]
Samanta, Supravat [1 ]
Adimurthy, Subbarayappa [1 ]
机构
[1] CSIR, Cent Salt & Marine Chem Res Inst, Acad Sci & Innovat Res Proc Design & Engn Cell, Bhavnagar 364002, Gujarat, India
关键词
H BOND FUNCTIONALIZATION; PYRROLE SYNTHESIS; 3+2 CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; SUBSTITUTED PYRROLES; OXIDATIVE LINKAGE; C-N; ALKYNES; FACILE; 2H-AZIRINES;
D O I
10.1039/c5ob01407g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed C(sp(3))-H functionalization of ketones with vinyl azides for the synthesis of substituted pyrroles has been developed. The method is a straightforward and efficient way to access a series of 2,3,5-trisubstituted-1H-pyrroles in modest to excellent yields with broad functional group tolerance under mild conditions.
引用
收藏
页码:10113 / 10116
页数:4
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共 56 条
[11]  
Fan XS, 2003, CHINESE J CHEM, V21, P336
[12]   Chemistry and biology of roseophilin and the prodigiosin alkaloids:: A survey of the last 2500 years [J].
Fürstner, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3582-3603
[13]  
FURSTNER A, 1995, J ORG CHEM, V60, P6637
[14]  
Gemma EV., 2008, SYNLETT, P2597
[15]   A facile and efficient synthesis of multisubstituted pyrroles from enaminoesters and nitroolefins [J].
Guan, Zheng-Hui ;
Li, Liang ;
Ren, Zhi-Hui ;
Li, Jianli ;
Zhao, Mi-Na .
GREEN CHEMISTRY, 2011, 13 (07) :1664-1668
[16]   Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles [J].
Gulevich, Anton V. ;
Dudnik, Alexander S. ;
Chernyak, Natalia ;
Gevorgyan, Vladimir .
CHEMICAL REVIEWS, 2013, 113 (05) :3084-3213
[17]  
Hantzsch A., 1890, BER DTSCH CHEM GES, V23, P1474, DOI [10.1002/cber.189002301243, DOI 10.1002/CBER.189002301243]
[18]  
Knorr L., 1884, CHEM BER-RECL, V17, P1635, DOI [DOI 10.1002/CBER.18840170220, 10.1002/cber.18840170220]
[19]   Ruthenium-Catalyzed Pyrrole Synthesis via Oxidative Annulation of Enamides and Alkynes [J].
Li, Bin ;
Wang, Nuancheng ;
Liang, Yujie ;
Xu, Shansheng ;
Wang, Baiquan .
ORGANIC LETTERS, 2013, 15 (01) :136-139
[20]   Cu-Catalyzed Ring Opening Reaction of 2H-Azirines with Terminal Alkynes: An Easy Access to 3-Alkynylated Pyrroles [J].
Li, Tengfei ;
Xin, Xiaoyi ;
Wang, Chunxiang ;
Wang, Dongping ;
Wu, Fan ;
Li, Xincheng ;
Wan, Boshun .
ORGANIC LETTERS, 2014, 16 (18) :4806-4809