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

被引：76

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

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 08期

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

页码：1469 / 1472

页数：4

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
Barn, D
Caulfield, W
Cowley, P
Dickins, R
Bakker, WI
McGuire, R
Morphy, JR
Rankovic, Z
Thorn, M
[J]. 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
BIRKOFER, L
FRANZ, M
[J]. CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (05): : 1759 - &
[5] Solid-phase synthesis of functionalized 1,2,3-triazoles
Blass, BE
Coburn, KR
Faulkner, AL
Hunn, CL
Natchus, MG
Parker, MS
Portlock, DE
Tullis, JS
Wood, R
[J]. TETRAHEDRON LETTERS, 2002, 43 (22) : 4059 - 4061
[6] Synthesis of tertiary amines using a polystyrene (REM) resin
Brown, AR
Rees, DC
Rankovic, Z
Morphy, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) : 3288 - 3295
[7] Optimization of reaction conditions for REM resin-bound quaternization reactions
Cameron, KS
Morphy, JR
Rankovic, Z
York, M
[J]. 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
Feldman, AK
Colasson, B
Fokin, VV
[J]. 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
HLASTA, DJ
ACKERMAN, JH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6184 - 6189

← 1 2 →