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1-(2,6-二氯-4-三氟甲基苯基)-4-烷基-1H-[1,2,3]-三唑的区域选择性合成

Regioselective synthesis of 1-(2,6-dichloro-4-trifluoromethylphenyl)- 4-alkyl-1H-[1,2,3]-triazoles.

作者信息

Hu Huanan, Zhang Anjiang, Ding Lisheng, Lei Xinxiang, Zhang Lixue

机构信息

Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, PR China.

出版信息

Molecules. 2008 Mar 3;13(3):556-66. doi: 10.3390/molecules13030556.

Abstract

A new and efficient method for the synthesis of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-alkyl-1H-[1,2,3]-triazoles by the room temperature 1,3-dipolar cycloaddition of (2-azido-1,3-dichloro-5-trifluoromethyl)benzene with terminal alkynes in the presence of Cu (I) salt as catalyst is reported. All the reactions gave 1,4-disubstituted products with high regioselectivity, as no 1,5-disubstituted product was formed. The structures of all the title compounds have been confirmed by elemental analysis, 1H- and 13C-NMR and in addition, the structure of compound 5a was investigated by X-ray crystallography.

摘要

报道了一种通过在室温下,以Cu(I)盐为催化剂,使(2-叠氮基-1,3-二氯-5-三氟甲基)苯与末端炔烃进行1,3-偶极环加成反应,来合成1-(2,6-二氯-4-三氟甲基苯基)-4-烷基-1H-[1,2,3]-三唑的新的高效方法。所有反应均以高区域选择性得到1,4-二取代产物,因为未形成1,5-二取代产物。所有标题化合物的结构均已通过元素分析、1H-和13C-NMR得到证实,此外,化合物5a的结构通过X射线晶体学进行了研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/75b1/6244963/bad35827b0da/molecules-13-00556-g002.jpg

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