An efficient and facile one-pot synthesis of propargylamines by three-component coupling of aldehydes, amines, and alkynes via C-H activation catalyzed by NiCl2

被引:140
作者
Samai, Subhasis [1 ]
Nandi, Ganesh Chandra [1 ]
Singh, M. S. [1 ]
机构
[1] Banaras Hindu Univ, Fac Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
关键词
Three-component A(3)-coupling; C-H bond activation; NiCl2; Propargylamines; Aldehydes; Amines; DIRECT-ADDITION; MULTICOMPONENT REACTIONS; TERMINAL ALKYNES; REUSABLE CATALYST; COPPER; SILVER; COMPLEX; CONDENSATION; ALKYNYLATION; IMINES;
D O I
10.1016/j.tetlet.2010.08.043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
NiCl2 was found to be a highly efficient and effective catalyst for the one-pot three-component (A(3)) coupling of aldehydes, amities, and alkynes to produce propargylamines in nearly quantitative yields. Structurally divergent aldehydes, amines, and alkynes were converted into the corresponding propargylamines. No co-catalyst or activator is needed and water is the only byproduct of this novel protocol. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5555 / 5558
页数:4
相关论文
共 88 条
[1]   Impregnated copper on magnetite: an efficient and green catalyst for the multicomponent preparation of propargylamines under solvent free conditions [J].
Aliaga, Maria J. ;
Ramon, Diego J. ;
Yus, Miguel .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (01) :43-46
[2]   A new method for the synthesis of functionalized maleimides [J].
Alizadeh, Abdolali ;
Movahedi, Farnaz ;
Esmaili, Abbas Ali .
TETRAHEDRON LETTERS, 2006, 47 (26) :4469-4471
[3]  
[Anonymous], ORGANOMAGNESIUM METH
[4]  
[Anonymous], ORGANOLITHIUM METHOD
[5]   INCREASED LIFE EXPECTANCY RESULTING FROM ADDITION OF L-DEPRENYL TO MADOPAR TREATMENT IN PARKINSONS-DISEASE - A LONGTERM STUDY [J].
BIRKMAYER, W ;
KNOLL, J ;
RIEDERER, P ;
YOUDIM, MBH ;
HARS, V ;
MARTON, J .
JOURNAL OF NEURAL TRANSMISSION, 1985, 64 (02) :113-127
[6]   Enantioselective one-pot three-component synthesis of propargylamines [J].
Bisai, Alakesh ;
Singh, Vinod K. .
ORGANIC LETTERS, 2006, 8 (11) :2405-2408
[7]   Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from Methyleneaziridines Using a Four-Component Reaction [J].
Cariou, Claire C. A. ;
Clarkson, Guy J. ;
Shipman, Michael .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (24) :9762-9764
[8]   Comprehensive review of rasagiline, a second-generation monoamine oxidase inhibitor, for the treatment of Parkinson's disease [J].
Chen, Jack J. ;
Swope, David M. ;
Dashtipour, Khashayar .
CLINICAL THERAPEUTICS, 2007, 29 (09) :1825-1849
[9]   Iron-catalyzed three-component coupling of aldehyde, alkyne, and amine under neat conditions in air [J].
Chen, Wen-Wen ;
Nguyen, Rene V. ;
Li, Chao-Jun .
TETRAHEDRON LETTERS, 2009, 50 (24) :2895-2898
[10]   Hydroxyapatite supported copper catalyst for effective three-component coupling [J].
Choudary, BM ;
Sridhar, C ;
Kantam, ML ;
Sreedhar, B .
TETRAHEDRON LETTERS, 2004, 45 (39) :7319-7321