Synthesis of phenylacetylene containing 1,2,3-triazole group

被引：4
|
作者：
Zhang, Wensheng [1 ,2 ]
Su, Changhui [1 ]
Jiang, Yubo [1 ]
Kuang, Chunxiang [1 ]
机构：
[1] Tongji Univ, Dept Chem, Shanghai 200092, Peoples R China
[2] Jiaozuo Teachers Coll, Dept Chem, Jiaozuo 454001, Peoples R China
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2009年 / 35卷 / 05期
关键词：
1,2,3-Triazole; Cinnamic acid; (Z)-Arylvinyl bromides; Arylacetylene; Microwave irradiation; CROSS-COUPLING REACTIONS; SITU CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION; TERMINAL ALKYNES; DRUG DISCOVERY; SOLID-PHASE; AZIDES; PEPTIDOTRIAZOLES; ANTAGONISTS; CONVENIENT;
D O I：
10.1007/s11164-009-0065-1
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Bromination of (E)-1-[4-(2-carboxy-vinyl)phenyl]-[1,2,3]triazole-4-carboxylic acid ethyl ester, which was synthesized in 90% yield by a Huisgen-type [3 + 2]-cycloaddition reaction between 3-(4-azidophenyl) acrylic acid and ethyl propiolate, in CHCl3 followed by a debrominative decarboxylation reaction with Et3N in DMF under microwave irradiation condition afforded stereoselective (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in 94% yield. Treatment of (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester with EtONa in DMF afforded 1-(4-ethynylphenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in a yield of 90%.
引用
收藏
页码：589 / 595
页数：7
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