Magnetically Recoverable CuFe2O4 Nanoparticles: Catalyzed Synthesis of Aryl Azides and 1,4-Diaryl-1,2,3-triazoles from Boronic Acids in Water

被引:66
作者
Kumar, A. Suresh [1 ]
Reddy, M. Amarnath [1 ]
Knorn, M. [1 ,2 ]
Reiser, O. [2 ]
Sreedhar, B. [1 ]
机构
[1] CSIR, Inorgan & Phys Chem Div, Indian Inst Chem Technol, Hyderabad 500607, Andhra Pradesh, India
[2] Univ Regensburg, Dept Organ Chem, D-93053 Regensburg, Germany
关键词
Synthetic methods; Nanoparticles; Magnetic properties; Azides; Iron; ONE-POT SYNTHESIS; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; HETEROGENEOUS CATALYSTS; RECYCLABLE CATALYST; KINETIC RESOLUTION; COMBRETASTATIN A-4; REUSABLE CATALYST; TERMINAL ALKYNES; RAPID SYNTHESIS; AROMATIC RING;
D O I
10.1002/ejoc.201300343
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Magnetically recoverable and reusable CuFe2O4 nanoparticles are shown to be highly efficient catalysts for the one-pot synthesis of biologically important 1,4-diaryl-1,2,3-triazoles starting from boronic acids, sodium azide, and acetylenes. The use of aqueous reaction medium at room temperature, the low cost and facile recovery of the catalyst by application of an external magnetic field, and consistently high catalytic efficiency for at least three consecutive cycles renders the protocol operationally attractive.
引用
收藏
页码:4674 / 4680
页数:7
相关论文
共 80 条
[1]   1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].
ALVAREZ, R ;
VELAZQUEZ, S ;
SANFELIX, A ;
AQUARO, S ;
DECLERCQ, E ;
PERNO, CF ;
KARLSSON, A ;
BALZARINI, J ;
CAMARASA, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194
[2]  
Anastas P., 1998, GREEN CHEM THEORY PR
[3]   Efficient one-pot synthesis of 1-aryl 1,2,3-triazoles from aryl halides and terminal alkynes in the presence of sodium azide [J].
Andersen, J ;
Bolvig, S ;
Liang, XF .
SYNLETT, 2005, (19) :2941-2947
[4]   Rapid synthesis of aryl azides from aryl halides under mild conditions [J].
Andersen, J ;
Madsen, U ;
Björkling, F ;
Liang, XF .
SYNLETT, 2005, (14) :2209-2213
[5]  
[Anonymous], 2010, Angew. Chem., DOI DOI 10.1002/ANGE.200905684
[6]   Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry [J].
Aucagne, Vincent ;
Leigh, David A. .
ORGANIC LETTERS, 2006, 8 (20) :4505-4507
[7]  
Avudoddi V., 2012, EUR J CHEM, V3, P298
[8]   Magnetically retrievable catalysts for organic synthesis [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
CHEMICAL COMMUNICATIONS, 2013, 49 (08) :752-770
[9]   Synthesis and Antiprotozoal Activity of Cationic 1,4-Diphenyl-1H-1,2,3-triazoles [J].
Bakunov, Stanislav A. ;
Bakunova, Svetlana M. ;
Wenzler, Tanja ;
Ghebru, Maedot ;
Werbovetz, Karl A. ;
Brun, Reto ;
Tidwell, Richard R. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (01) :254-272
[10]   D-ring substituted 1,2,3-triazolyl 20-keto pregnenanes as potential anticancer agents: Synthesis and biological evaluation [J].
Banday, Abid H. ;
Shameem, Shameem A. ;
Gupta, B. D. ;
Kumar, H. M. Sampath .
STEROIDS, 2010, 75 (12) :801-804