One-Pot, Three-Component Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles Starting from Primary Alcohols

被引：23

作者：

Jin, Guanyi ^{[1
]}

Zhang, Jian ^{[1
]}

Fu, Dan ^{[1
]}

Wu, Jingjing ^{[1
]}

Cao, Song ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 28期

基金：

国家高技术研究发展计划(863计划); 中国国家自然科学基金;

关键词：

Multicomponent reactions; Nitrogen heterocycles; Alcohols; Ketones; RUTHENIUM-CATALYZED CYCLOADDITION; AZIDE-ALKYNE CYCLOADDITION; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; CLICK CHEMISTRY; DIRECT ARYLATION; ORGANIC AZIDES; TRIAZOLE; DESIGN;

D O I：

10.1002/ejoc.201200830

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, one-pot, three-component approach for the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles through the cycloaddition of a wide range of primary alcohols with sodium azide and active methylene ketones in the presence of N-(p-toluenesulfonyl)imidazole, tetrabutylammonium iodide, and triethylamine in DMF/DMSO has been developed.

引用

页码：5446 / 5449

页数：4

共 50 条

[41] One-pot parallel synthesis of 1,3,5-trisubstituted 1,2,4-triazoles
Dmytro S. Radchenko
Vasyl S. Naumchyk
Igor Dziuba
Andrii A. Kyrylchuk
Kateryna E. Gubina
Yurii S. Moroz
Oleksandr O. Grygorenko
Molecular Diversity, 2022, 26 : 993 - 1004
[42] Copper(I)-Catalyzed Interrupted Click Reaction: Synthesis of 1,4,5-Trisubstituted 5-Chloro-1,2,3-Triazoles
Wu, Qiming
Song, Wangze
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (42)
[43] One-pot parallel synthesis of 1,3,5-trisubstituted 1,2,4-triazoles
Radchenko, Dmytro S.
Naumchyk, Vasyl S.
Dziuba, Igor
Kyrylchuk, Andrii A.
Gubina, Kateryna E.
Moroz, Yurii S.
Grygorenko, Oleksandr O.
MOLECULAR DIVERSITY, 2022, 26 (02) : 993 - 1004
[44] One-pot three-component synthesis of 1,2,3-triazoles using magnetic NiFe2O4-glutamate-Cu as an efficient heterogeneous catalyst in water
Lu, Jun
Ma, Er-Qian
Liu, Yu-Heng
Li, Ya-Meng
Mo, Li-Ping
Zhang, Zhan-Hui
RSC ADVANCES, 2015, 5 (73): : 59167 - 59185
[45] Stereoselective Synthesis of Phenyl-1,2,3-triazoles Containing (E)-Vinyl Halide Group via a One-Pot, Three-Component Reaction
Zhang, Wensheng
Su, Changhui
Kuang, Chunxiang
Yang, Qing
SYNTHETIC COMMUNICATIONS, 2011, 41 (09) : 1267 - 1275
[46] One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Aldehydes and Amines
Maisonneuve, Stephane
Xie, Juan
SYNLETT, 2009, (18) : 2977 - 2981
[47] One-pot three component synthesis of 5-allyl-1,2,3-triazoles using copper(I) acetylides
Reddy, Parigi Raghavendar
Cui, Lianji
Ryu, Jae-Sang
RSC ADVANCES, 2018, 8 (05): : 2759 - 2767
[48] Efficient synthesis of allylic azides and one-pot regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles from homoallyl alcohols
Reddy, P. Surendra
Ravi, V.
Sreedhar, B.
TETRAHEDRON LETTERS, 2010, 51 (31) : 4037 - 4041
[49] A Facile One-Pot Metal-Free Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
Jia, Qianfa
Yang, Gongming
Chen, Lei
Du, Zhiyun
Wei, Jia
Zhong, Yanqiong
Wang, Jian
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (16) : 3435 - 3440
[50] Synthesis of 1,4,5-trisubstituted-1,2,3-triazoles via coupling reaction of diaminomaleonitrile with aromatic diazonium salts
Al-Azmi, Amal
Kalarikkal, Anita K.
TETRAHEDRON, 2013, 69 (52) : 11122 - 11129

← 1 2 3 4 5 →