An Efficient, One-Pot, Regioselective Synthesis of 1,4-Diaryl-1H-1,2,3-triazoles Using Click Chemistry

被引:50
作者
Kumar, Dalip [1 ]
Reddy, Vaddula Buchi [1 ]
机构
[1] Birla Inst Technol & Sci, Chem Grp, Pilani 333031, Rajasthan, India
来源
SYNTHESIS-STUTTGART | 2010年 / 10期
关键词
1,4-diaryl-1H-1,2,3-triazoles; click chemistry; diaryliodonium salts; aryl azides; cycloaddition; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; DIARYLIODONIUM SALTS; 3+2 CYCLOADDITION; TERMINAL ALKYNES; AROMATIC-AMINES; SODIUM-AZIDE; ARYL HALIDES; TRIAZOLE; ACETYLENES; CONVERSION;
D O I
10.1055/s-0029-1218765
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, one-pot, regioselective synthesis of 1,4-diaryl-1H-1,2,3-triazoles is described via the copper(I)-catalyzed reaction of diaryliodonium salts, sodium azide and terminal alkynes. The generality of this protocol is demonstrated by the synthesis of a series of 1,4-diaryl-1H-1,2,3-triazoles in good to high yields. The catalyst and reaction solvent are reused without any appreciable reduction in product yield.
引用
收藏
页码:1687 / 1691
页数:5
相关论文
共 43 条
[1]  
Agrawal J.P., 2007, Organic Chemistry of Explosives
[2]   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
[3]   Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3+2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions [J].
Amantini, D ;
Fringuelli, F ;
Piermatti, O ;
Pizzo, F ;
Zunino, E ;
Vaccaro, L .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6526-6529
[4]   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
[5]   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
[6]   Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].
Barral, Karine ;
Moorhouse, Adam D. ;
Moses, John E. .
ORGANIC LETTERS, 2007, 9 (09) :1809-1811
[7]   Kinugasa reaction under click chemistry conditions [J].
Basak, A. ;
Chandra, K. ;
Pal, R. ;
Ghosh, S. C. .
SYNLETT, 2007, (10) :1585-1588
[8]   Azide/alkyne-"click" reactions: Applications in material science and organic synthesis [J].
Binder, Wolfgang H. ;
Kluger, Christian .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (14) :1791-1815
[9]   REACTIONS OF SODIUM PHENYLACETYLIDE AND SODIUM ALKOXIDE WITH TOSYL AND MESYL AZIDES [J].
BOYER, JH ;
MACK, CH ;
GOEBEL, N ;
MORGAN, LR .
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (07) :1051-1053
[10]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240