Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition

被引：71

作者：

Harju, K

Vahermo, M

Mutikainen, I

Yli-Kauhaluoma, J

机构：

[1] Univ Helsinki, Dept Pharm, Viikki Drug Discovery Technol Ctr, FIN-00014 Helsinki, Finland

[2] Univ Helsinki, Dept Chem, Inorgan Chem Lab, FIN-00014 Helsinki, Finland

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/cc030110c

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition of polymer-bound azides to various alkynes is reported. Polymer-bound azides were synthesized from polymer-bound halides and sodium azide and reacted with alkynes to produce polymer-bound 1,2,3-triazoles. Cleavage of the triazoles was performed with trifluoroacetic acid. A traceless synthesis of 1,2,3-triazoles was developed using 2-methoxy-substituted resin (polymer-bound 4-hydroxy-2-methoxybenzyl alcohol). In addition, a synthesis of 4-hydroxybenzyl-substituted 1,2,3-triazoles from the bromo-Wang resin (4-(bromomethyl)phenoxymethyl polystyrene) was achieved.

引用

收藏

页码：826 / 833

页数：8

相关论文

共 47 条

[1] DIPOLAR CYCLO-ADDITION REACTIONS OF ORGANIC AZIDES WITH SOME ACETYLENIC-COMPOUNDS [J].

ABUORABI, ST ;

ATFAH, MA ;

JIBRIL, I ;

MARII, FM ;

ALI, AAS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (05) :1461-1468

[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]

BIAGI G, 1985, EUR J MED CHEM, V20, P267

[4]

BIAGI G, 1990, FARMACO, V45, P1181

[5]

BIAGI G, 1986, FARMACO, V41, P597

[6] Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core [J].

Bilodeau, MT ;

Cunningham, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2800-2801

[7] 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

[8] BENZYLATED 1,2,3-TRIAZOLES AS ANTICOCCIDIOSTATS [J].

BOCHIS, RJ ;

CHABALA, JC ;

HARRIS, E ;

PETERSON, LH ;

BARASH, L ;

BEATTIE, T ;

BROWN, JE ;

GRAHAM, DW ;

WAKSMUNSKI, FS ;

TISCHLER, M ;

JOSHUA, H ;

SMITH, J ;

COLWELL, LF ;

WYVRATT, MJ ;

FISHER, MH ;

TAMAS, T ;

NICOLICH, S ;

SCHLEIM, KD ;

WILKS, G ;

OLSON, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2843-2852

[9] STUDIES ON V-TRIAZOLES .4. THE 4-METHOXYBENZYL GROUP, A VERSATILE N-PROTECTING GROUP FOR THE SYNTHESIS OF N-UNSUBSTITUTED V-TRIAZOLES [J].

BUCKLE, DR ;

ROCKELL, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02) :627-630

[10] The universal Rink-isonitrile resin: applications in Ugi reactions [J].

Chen, JJ ;

Golebiowski, A ;

Klopfenstein, SR ;

West, L .

TETRAHEDRON LETTERS, 2002, 43 (22) :4083-4085

← 1 2 3 4 5 →