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

被引:140
作者
Amantini, D [1 ]
Fringuelli, F [1 ]
Piermatti, O [1 ]
Pizzo, F [1 ]
Zunino, E [1 ]
Vaccaro, L [1 ]
机构
[1] Univ Perugia, CEMIN, Dipartimento Chim, I-06123 Perugia, Italy
关键词
D O I
10.1021/jo0507845
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-eyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glassware or inert atmosphere.
引用
收藏
页码:6526 / 6529
页数:4
相关论文
共 68 条
[41]   1.3-DIPOLARE CYCLOADDITIONEN .23. EINIGE BEOBACHTUNGEN ZUR ADDITION ORGANISCHER AZIDE AN CC-DREIFACHBINDUNGEN [J].
HUISGEN, R ;
KNORR, R ;
MOBIUS, L ;
SZEIMIES, G .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (12) :4014-&
[42]   Highly efficient and mild synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives [J].
Journet, M ;
Cai, DW ;
Kowal, JJ ;
Larsen, RD .
TETRAHEDRON LETTERS, 2001, 42 (52) :9117-9118
[43]   Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst [J].
Kamijo, S ;
Jin, TN ;
Huo, ZB ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7786-7787
[44]   Synthesis of C-carbamoyl-1,2,3-triazoles by microwave-induced 1,3-dipolar cycloaddition of organic azides to acetylenic amides [J].
Katritzky, AR ;
Singh, SK .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :9077-9079
[45]  
KIRMSE W, 1958, LIEBIGS ANN CHEM, V614, P1
[46]   Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited [J].
Krasinski, A ;
Fokin, VV ;
Sharpless, KB .
ORGANIC LETTERS, 2004, 6 (08) :1237-1240
[48]  
Lewis WG, 2002, ANGEW CHEM INT EDIT, V41, P1053, DOI 10.1002/1521-3773(20020315)41:6<1053::AID-ANIE1053>3.0.CO
[49]  
2-4
[50]  
MAIORANA S, 1966, TETRAHEDRON LETT, P6043