Tandem azidination- and hydroazidination-Huisgen [3+2] cycloadditions of ynamides. Synthesis of chiral amide-substituted triazoles

被引:42
作者
Zhang, Xuejun
Hsung, Richard P.
You, Lingfeng
机构
[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA
[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA
关键词
D O I
10.1039/b606680a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tandem azidination - and hydroazidination - Huisgen [ 3 + 2] cycloadditions of ynamides are described here. These processes are regioselective and chemoselective, leading to the synthesis of chiral amide-substituted triazoles.
引用
收藏
页码:2679 / 2682
页数:4
相关论文
共 77 条
[71]   Indium(III) triflate catalyzed tandem azidation/1,3-dipolar cycloaddition reaction of ω,ω-dialkoxyalkyne derivatives with trimethylsilyl azide [J].
Yanai, H ;
Taguchi, T .
TETRAHEDRON LETTERS, 2005, 46 (50) :8639-8643
[72]   Ruthenium-catalyzed cycloaddition of alkynes and organic azides [J].
Zhang, L ;
Chen, XG ;
Xue, P ;
Sun, HHY ;
Williams, ID ;
Sharpless, KB ;
Fokin, VV ;
Jia, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :15998-15999
[73]   Syntheses of vinylindoles via a Bronsted acid catalyzed highly regio- and stereoselective cis-hydroarylation of ynamides [J].
Zhang, Y .
TETRAHEDRON LETTERS, 2005, 46 (38) :6483-6486
[74]   Bronsted acid-catalyzed highly stereoselective arene-ynamide cyclizations.: A novel keteniminium Pictet-Spengler cyclization syntheses of (±)-desbromoarborescidines A and C [J].
Zhang, YS ;
Hsung, RP ;
Zhang, XJ ;
Huang, J ;
Slafer, BW ;
Davis, A .
ORGANIC LETTERS, 2005, 7 (06) :1047-1050
[75]   Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides [J].
Zhang, YS ;
Hsung, RP ;
Tracey, MR ;
Kurtz, KCM ;
Vera, EL .
ORGANIC LETTERS, 2004, 6 (07) :1151-1154
[76]   Synthesis of aryl azides and vinyl azides via proline-promoted CuI-catalyzed coupling reactions [J].
Zhu, W ;
Ma, DW .
CHEMICAL COMMUNICATIONS, 2004, (07) :888-889
[77]   Recent advances in the chemistry of ynamines and ynamides [J].
Zificsak, CA ;
Mulder, JA ;
Hsung, RP ;
Rameshkumar, C ;
Wei, LL .
TETRAHEDRON, 2001, 57 (36) :7575-7606