- Direct Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- And Azide-Free Conditions
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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
- Geng, Xiao,Huang, Chun,Wang, Li-Sheng,Wu, An-Xin,Wu, Yan-Dong,Yu, Xiao-Xiao,Zhao, Peng,Zhou, You
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p. 13664 - 13672
(2021/10/01)
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- Magnetically separable ZnFe2O4 nanoparticles: A low cost and sustainable catalyst for propargyl amine and NH-triazole synthesis
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The multicomponent reaction (MCR) strategy for the construction of important molecular scaffolds is in trending nowadays and among them, A3-coupling stands in a significant position. Aldehyde, amine and alkynes are coupled in this particular reaction via C-H activation process. Herein, we have reported zinc ferrite nanoparticles as magnetically separable heterogeneous catalyst for A3-coupling reaction with attractive attributes like excellent productivity, selectivity and better reusability. Moreover, the catalyst can also be effectively applied for the synthesis of various NH-triazoles with quantitative yields of the products. A plausible mechanism has been proposed for the synthesis of NH-triazoles followed by validation with computational study.
- Bordoloi, Ankur,Chetia, Swadhin,Garg, Anirban,Guha, Ankur Kanti,Hazarika, Roktopol,Kalita, Amlan Jyoti,Kulshrestha, Akshay,Kumar, Arvind,Phukan, Parmita,Sarma, Diganta
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- Iodine-Mediated Condensation–Cyclization of α-Azido Ketones with p-Toluenesulfonyl Hydrazide for Synthesis of 4-Aryl-NH-1,2,3-Triazoles
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A molecular iodine mediated condensation–cyclization reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed from readily available α-azido acetophenones and p-toluenesulfonyl hydrazide. This reaction provides a metal-free strategy for the sequential formation of C–N and N–N bonds in mild condition.
- Ren, Ming-Tian,Li, Min,Wang, An-Jing,Gao, Jie,Zhang, Xiang-Xiang,Shu, Wen-Ming
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supporting information
p. 2233 - 2236
(2020/04/16)
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- Metal-Free Cascade [4 + 1] Cyclization Access to 4-Aryl- NH-1,2,3-triazoles from N-Tosylhydrazones and Sodium Azide
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A molecular iodine-mediated coupling cyclization reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed from N-tosylhydrazones and sodium azide. This metal-free cascade [4 + 1] cyclization reaction could rapidly synthesize valuable com
- Shu, Wen-Ming,Zhang, Xun-Fang,Zhang, Xiang-Xiang,Li, Min,Wang, An-Jing,Wu, An-Xin
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p. 14919 - 14925
(2019/11/11)
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- Method of catalytically synthesizing 4-aryl-NH-1,2,3-triazole derivative under microwave radiation
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The invention discloses a method of catalytically synthesizing 4-aryl-NH-1,2,3-triazole derivative under microwave radiation. The method includes the steps of: successively adding substituted 2-nitroolefin, sodium azide, TfOH, and pyridine into a reaction
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Paragraph 0011; 0038
(2018/03/26)
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- One-Pot Synthesis of 4-Aryl-NH-1,2,3-Triazoles through Three-Component Reaction of Aldehydes, Nitroalkanes and NaN3
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A one-pot three-component reaction of aldehydes, nitroalkanes and NaN3 for the synthesis of NH-1,2,3-triazoles has been developed. The reaction provides a safe, efficient and step-economic approach for the synthesis of various NH-1,2,3-triazoles in good to excellent yields.
- Hui, Rongrong,Zhao, Mina,Chen, Ming,Ren, Zhihui,Guan, Zhenghui
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p. 1808 - 1812
(2017/09/06)
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- 4-Aryl- NH -1,2,3-Triazoles via Multicomponent Reaction of Aldehydes, Nitroalkanes, and Sodium Azide
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4-Aryl-NH-1,2,3-triazoles are valuable compounds in organic chemistry and pharmaceutical chemistry. In this paper, we describe a novel multicomponent reaction of aldehydes, nitroalkanes, and sodium azide for the synthesis of 4-aryl-NH-1,2,3-triazoles. In this transformation, it was found that both the slow addition of nitroalkane and the presence of NaHSO3/Na2SO3 are advantageous to promote the reaction results. Additionally, a series of aldehydes and nitro compounds were investigated.
- Wu, Luyong,Wang, Xianghui,Chen, Yuxue,Huang, Qinglan,Lin, Qiang,Wu, Mingshu
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p. 437 - 441
(2016/02/09)
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- Direct Synthesis of N-Unsubstituted 4-Aryl-1,2,3-triazoles Mediated by Amberlyst-15
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A highly efficient and effective method for the synthesis of N-unsubstituted 4-aryl-1,2,3-triazoles promoted by Amberlyst-15 is described. The promoter can be recycled and reused up to eight times without any reduction in its catalytic activity.
- Zhang, Hui,Dong, Dao-Qing,Wang, Zu-Li
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p. 131 - 135
(2015/12/26)
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- Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition
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Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.
- R?hrig, Ute F.,Majjigapu, Somi Reddy,Grosdidier, Aurélien,Bron, Sylvian,Stroobant, Vincent,Pilotte, Luc,Colau, Didier,Vogel, Pierre,Van Den Eynde, Beno?t J.,Zoete, Vincent,Michielin, Olivier
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experimental part
p. 5270 - 5290
(2012/08/28)
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