Direct Synthesis of 4-Aryl-1,2,3-triazoles via l2-Promoted Cyclization under Metal- and Azide-Free Conditions

被引：17

作者：

Huang, Chun ^{[1
]}

Geng, Xiao ^{[2
,3
]}

Zhao, Peng ^{[1
]}

Zhou, You ^{[1
]}

Yu, Xiao-Xiao ^{[1
]}

Wang, Li-Sheng ^{[1
]}

Wu, Yan-Dong ^{[1
]}

Wu, An-Xin ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China

[2] Taizhou Univ, Adv Res Inst, Taizhou 318000, Zhejiang, Peoples R China

[3] Taizhou Univ, Dept Chem, Taizhou 318000, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 19期

基金：

中国国家自然科学基金;

关键词：

CATALYZED SYNTHESIS; SODIUM-AZIDE; CYCLOADDITION; 1H-1,2,3-TRIAZOLES; 1,2,3-TRIAZOLES; UREAS;

D O I：

10.1021/acs.joc.1c01702

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved using p-toluenesulfonyl hydrazines and 1-aminopyridinium iodide as azide surrogates, providing a novel route toNH-1,2,3-triazoles. Furthermore, this approach provides rapid and practical access to potent inhibitors of indoleamine 2,3-dioxygenase (IDO).

引用

页码：13664 / 13672

页数：9

共 48 条

[1] Abboud JLM, 2001, EUR J ORG CHEM, V2001, P3013
[2] Adibekian A, 2011, NAT CHEM BIOL, V7, P469, DOI [10.1038/nchembio.579, 10.1038/NCHEMBIO.579]
[3] Sulfenyl Ynamides in Gold Catalysis: Synthesis of Oxo-functionalised 4-aminoimidazolyl Fused Compounds by Intermolecular Annulation Reactions
Arce, Elsa M.
Lamont, Scott G.
Davies, Paul W.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (12) : 2503 - 2509
[4] Click Dendrimers and Triazole-Related Aspects: Catalysts, Mechanism, Synthesis, and Functions. A Bridge between Dendritic Architectures and Nanomaterials
Astruc, Didier
Liang, Liyuan
Rapakousiou, Amalia
Ruiz, Jaime
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (04) : 630 - 640
[5] Developments in Pd catalysis:: Synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides
Barluenga, Jose
Valdes, Carlos
Beltran, Gustavo
Escribano, Maria
Aznar, Fernando
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (41) : 6893 - 6896
[6] Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems
Chattopadhyay, Buddhadeb
Gevorgyan, Vladimir
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 862 - 872
[7] Conformational control in the regioselective synthesis of N-2-substituted-1,2,3-triazoles
Chen, Yunfeng
Liu, Yuxiu
Petersen, Jeffrey L.
Shi, Xiaodong
[J]. CHEMICAL COMMUNICATIONS, 2008, (28) : 3254 - 3256
[8] Metal-Free C-N- and N-N-Bond Formation: Synthesis of 1,2,3-Triazoles from Ketones, N-Tosylhydrazines, and Amines in One Pot
Chen, Zhengkai
Yan, Qiangqiang
Liu, Zhanxiang
Zhang, Yuhong
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) : 17635 - 17639
[9] Copper-Mediated Synthesis of 1,2,3-Triazoles from N-Tosylhydrazones and Anilines
Chen, Zhengkai
Yan, Qiangqiang
Liu, Zhanxiang
Xu, Yiming
Zhang, Yuhong
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13324 - 13328
[10] A Scalable Metal-, Azide-, and Halogen-Free Method for the Preparation of Triazoles
Clark, Peter R.
Williams, Glynn D.
Hayes, Jerome F.
Tomkinson, Nicholas C. O.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (17) : 6740 - 6744

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