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 50 条

[1] Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition
Harju, K
Vahermo, M
Mutikainen, I
Yli-Kauhaluoma, J
JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (06): : 826 - 833
[2] [3+2] cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles
Gao, Yongnian
Lam, Yulin
ORGANIC LETTERS, 2006, 8 (15) : 3283 - 3285
[3] Synthesis of 1-(substituted benzyl)-1,2,3-triazoles by 1,3-dipolar cycloaddition reaction
Hu, YH
Liu, SL
Tong, QY
Huang, FR
Shen, YJ
Qi, HM
Du, L
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (10) : 1228 - 1232
[4] 1,3-Dipolar cycloaddition reactions of enaminones and azides: Synthesis of 4-acyl-1,2,3-triazoles and mechanistic studies
Gaspar, Francisco V.
Azevedo, Marcelo F. M. F.
Carneiro, Leonardo S. A.
Ribeiro, Samuel B.
Esteves, Pierre M.
Buarque, Camilla D.
TETRAHEDRON, 2022, 120
[5] 1,3-Dipolar Cycloaddition in the Synthesis of Novel Isoxazoline/Pyrazole Derivatives Bearing 1,2,3-Triazoles Moiety
Zeng, Yongming
Liu, Fangming
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (03) : 696 - 702
[6] An efficient and regiospecific synthesis of 1,5-diaryl-4-benzothiazolyl-1,2,3-triazoles by organocatalytic 1,3-dipolar cycloaddition reactions
Shu, Miaomiao
Ran, Liqiong
Liu, Kexiong
Yang, Wen
Wang, Qiuan
SYNTHETIC COMMUNICATIONS, 2020, 50 (12) : 1863 - 1870
[7] Regiospecific synthesis of 2-allyl-1,2,3-triazoles by palladium-catalyzed 1,3-dipolar cycloaddition
Kamijo, S
Jin, TN
Huo, ZB
Yamamoto, Y
TETRAHEDRON LETTERS, 2002, 43 (52) : 9707 - 9710
[8] Solid-phase synthesis of substituted 1,2,3-triazoles
Zaragoza, F
Petersen, SV
TETRAHEDRON, 1996, 52 (32) : 10823 - 10826
[9] 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
TETRAHEDRON LETTERS, 2002, 43 (22) : 4059 - 4061
[10] Synthesis of carbohydrate-derived 1,2,3-triazoles using 1,3-dipolar cycloaddition on a soluble polymer support
Freeze, S
Norris, P
HETEROCYCLES, 1999, 51 (08) : 1807 - 1817

← 1 2 3 4 5 →