Synthesis of 1-(Substituted benzyl)-1,2,3-triazoles by 1,3-Dipolar Cycloaddition Reaction

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (10): 1228-1232. Previous Articles Next Articles

1,3-偶极环加成反应合成1-(取代苄基)-1,2,3-三唑类化合物

扈艳红^*,a, 刘世领^b, 仝钦宇^a, 黄发荣^a, 沈永嘉^b, 齐会民^a, 杜磊^a

^a华东理工大学材料科学与工程学院上海 200237;
^b华东理工大学精细化工研究所上海 200237

收稿日期:2003-10-21 修回日期:2003-02-23 接受日期:2004-04-19 发布日期:2022-09-20
基金资助:
国家安全重大基础研究973 (No. 5131101)、国家高技术研究发展计划863 (No. 2002AA35103)和武器装备预研基金(No. 51412020103QT311)资助项目.

Synthesis of 1-(Substituted benzyl)-1,2,3-triazoles by 1,3-Dipolar Cycloaddition Reaction

HU Yan-Hong^*,a, LIU Shi-Ling^b, TONG Qin-Yu^a, HUANG Fa-Rong^a, SHEN Yong-Jia^b, QI Hui-Min^a, DU Lei^a

^aSchool of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237;
^bInstitute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237

Received:2003-10-21 Revised:2003-02-23 Accepted:2004-04-19 Published:2022-09-20
Contact: * E-mail: fhuanglab@ecust.edu.cn; Fax: 021-64253031.

Abstract

Benzyl azide, 4-methyl-benzyl azide, 4-cyano-benzyl azide, 4-fluoro-benzyl azide and 1,1'-bi-azidomethyl-4,4'-biphenyl were prepared by the nucleophilic substitution reaction of NaN₃ with substituted benzyl chlorides. The reaction rate was affected by the substitution groups at the phenyl ring, and electron-withdrawing groups could accelerate the rate. And 1,3-dipolar cycloaddition reaction of the azides with phenylacetylene wasstudied. The corresponding compounds (azides and 1,2,3-triazoles) were characterized with NMR, FT-IR and elementary analysis. The 1,2,3-triazoles were thermal stable. The addition rate depended onthe substitution groups of the azides (1,3-dipole), and the reactivities correlated with polar effects: phenyacetylene (dipolarophile) reacted faster with electron-poor azides and vice versa. The 1,3-dipolar cycloaddition reaction wasfound to be regioselective, and the 4-phenyl-1,2,3-triazoles were the major products in the two structural isomers of 1,2,3-triazoles obtained.

Key words: azide, phenylacetylene, 1,2,3-triazole, 1,3-dipolar cycloaddition reaction

Cite this article

HU Yan-Hong, LIU Shi-Ling, TONG Qin-Yu, HUANG Fa-Rong, SHEN Yong-Jia, QI Hui-Min, DU Lei. Synthesis of 1-(Substituted benzyl)-1,2,3-triazoles by 1,3-Dipolar Cycloaddition Reaction[J]. Chinese Journal of Organic Chemistry, 2004, 24(10): 1228-1232.

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1,3-偶极环加成反应合成1-(取代苄基)-1,2,3-三唑类化合物

Synthesis of 1-(Substituted benzyl)-1,2,3-triazoles by 1,3-Dipolar Cycloaddition Reaction

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