Microwave-assisted Synthesis of New 1,2,3-Triazoles Bearing an Isoxazole Ring by the Azide-alkyne Cycloaddition Click Chemistry

doi:10.1007/s40242-018-7298-8

高等学校化学研究 ›› 2018, Vol. 34 ›› Issue (2): 197-202.doi: 10.1007/s40242-018-7298-8

Microwave-assisted Synthesis of New 1,2,3-Triazoles Bearing an Isoxazole Ring by the Azide-alkyne Cycloaddition Click Chemistry

LI Jing¹, LIU Hongwei¹, MENG Fanyu¹, YAN Liuqing¹, SHI Yanpeng¹, ZHANG Yumin^1,2, GU Qiang^1,2

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. National-Local Joint Engineering Laboratory of In-situ Conversion, Drilling and Exploitation Technology for Oil Shale, Changchun 130021, P. R. China

收稿日期:2017-09-07 修回日期:2017-11-03 出版日期:2018-04-01 发布日期:2017-12-04
通讯作者: GU Qiang,E-mail:guq@jlu.edu.cn E-mail:guq@jlu.edu.cn

Microwave-assisted Synthesis of New 1,2,3-Triazoles Bearing an Isoxazole Ring by the Azide-alkyne Cycloaddition Click Chemistry

LI Jing¹, LIU Hongwei¹, MENG Fanyu¹, YAN Liuqing¹, SHI Yanpeng¹, ZHANG Yumin^1,2, GU Qiang^1,2

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. National-Local Joint Engineering Laboratory of In-situ Conversion, Drilling and Exploitation Technology for Oil Shale, Changchun 130021, P. R. China

Received:2017-09-07 Revised:2017-11-03 Online:2018-04-01 Published:2017-12-04
Contact: GU Qiang,E-mail:guq@jlu.edu.cn E-mail:guq@jlu.edu.cn

摘要/Abstract

摘要： A comparison synthesis of 1,2,3-triazoles bearing isoxazole ether was developed between conventional and microwave-assisted heating. Single/double 1,2,3-triazoles bearing isoxazole ether were synthesized by click reaction starting from substituted isoxazolyl alkyne compounds and substituted benzyl azide compounds or neopentylglycol diazide in the presence of copper(I) that in-situ generated. Herein, the effect of different catalysts on the yield was researched by conventional method, and the optimal catalyst was selected. The structures of all the synthesized compounds were confirmed by MS, FTIR, ¹H and ¹³C NMR spectroscopies. Moreover, the crystal structure of 5-{[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]methyl}-3-(4-fluorophenyl)isoxazole(2h) was determined.

关键词: Microwave-assisted heating, 1,2,3-Triazole, Isoxazole, Azide-alkyne, Click chemistry

Abstract: A comparison synthesis of 1,2,3-triazoles bearing isoxazole ether was developed between conventional and microwave-assisted heating. Single/double 1,2,3-triazoles bearing isoxazole ether were synthesized by click reaction starting from substituted isoxazolyl alkyne compounds and substituted benzyl azide compounds or neopentylglycol diazide in the presence of copper(I) that in-situ generated. Herein, the effect of different catalysts on the yield was researched by conventional method, and the optimal catalyst was selected. The structures of all the synthesized compounds were confirmed by MS, FTIR, ¹H and ¹³C NMR spectroscopies. Moreover, the crystal structure of 5-{[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]methyl}-3-(4-fluorophenyl)isoxazole(2h) was determined.

Key words: Microwave-assisted heating, 1,2,3-Triazole, Isoxazole, Azide-alkyne, Click chemistry

LI Jing, LIU Hongwei, MENG Fanyu, YAN Liuqing, SHI Yanpeng, ZHANG Yumin, GU Qiang. Microwave-assisted Synthesis of New 1,2,3-Triazoles Bearing an Isoxazole Ring by the Azide-alkyne Cycloaddition Click Chemistry[J]. 高等学校化学研究, 2018, 34(2): 197-202.

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Microwave-assisted Synthesis of New 1,2,3-Triazoles Bearing an Isoxazole Ring by the Azide-alkyne Cycloaddition Click Chemistry

Microwave-assisted Synthesis of New 1,2,3-Triazoles Bearing an Isoxazole Ring by the Azide-alkyne Cycloaddition Click Chemistry

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