Trimethylsilyl-directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles

被引:77
作者
Coats, SJ [1 ]
Link, JS [1 ]
Gauthier, D [1 ]
Hlasta, DJ [1 ]
机构
[1] Johnson & Johnson Pharmaceut Res & Dev LLC, Spring House, PA 19477 USA
关键词
D O I
10.1021/ol047637y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A regioselective method for the preparation of 1,5-trisubstituted H-1-1,2,3-triazoles via a 1,3-dipolar cycloaddition of 1-trimethylsilylacetylenes with organciazides is described. Immobilization of the azide on REM resin and subsequent cycloaddition afforded a 2 x 2 x 4 x 3 membered 1,5-disubstituted H-1-1,2,3-triazole library with an average purified yield of 68%.
引用
收藏
页码:1469 / 1472
页数:4
相关论文
共 17 条
[1]  
[Anonymous], 1974, ADV HETEROCYCLIC CHE
[2]   Design and synthesis of a maximally diverse and druglike screening library using REM resin methodology [J].
Barn, D ;
Caulfield, W ;
Cowley, P ;
Dickins, R ;
Bakker, WI ;
McGuire, R ;
Morphy, JR ;
Rankovic, Z ;
Thorn, M .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (06) :534-541
[3]  
BIRKHOFER L, 1972, CHEM BER, V105, P1767
[4]   ORGANOSILICON COMPOUNDS .50. SELECTIVE SUBSTITUTIONS IN C-SILYLPYRAZOLES [J].
BIRKOFER, L ;
FRANZ, M .
CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (05) :1759-&
[5]   Solid-phase synthesis of functionalized 1,2,3-triazoles [J].
Blass, BE ;
Coburn, KR ;
Faulkner, AL ;
Hunn, CL ;
Natchus, MG ;
Parker, MS ;
Portlock, DE ;
Tullis, JS ;
Wood, R .
TETRAHEDRON LETTERS, 2002, 43 (22) :4059-4061
[6]   Synthesis of tertiary amines using a polystyrene (REM) resin [J].
Brown, AR ;
Rees, DC ;
Rankovic, Z ;
Morphy, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3288-3295
[7]   Optimization of reaction conditions for REM resin-bound quaternization reactions [J].
Cameron, KS ;
Morphy, JR ;
Rankovic, Z ;
York, M .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (03) :199-203
[8]   One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides [J].
Feldman, AK ;
Colasson, B ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (22) :3897-3899
[9]  
GUILLERM G, 1973, B SOC CHIM FR II-CH, P2739
[10]   STERIC EFFECTS ON THE REGIOSELECTIVITY OF AN AZIDE-ALKYNE DIPOLAR CYCLOADDITION REACTION - THE SYNTHESIS OF HUMAN-LEUKOCYTE ELASTASE INHIBITORS [J].
HLASTA, DJ ;
ACKERMAN, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6184-6189