1178538-57-2Relevant articles and documents
Method for preparing 1,2,3-triazole compound by heterogeneous copper catalysis in one pot
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Paragraph 0050-0051; 0052-0055, (2019/12/25)
The invention relates to a method for preparing a 1-aryl-4-substituted-1,2,3-triazole compound shown as a formula (II). The method comprises the following steps: mixing arylboronic acid (1), NaN3, a heterogeneous copper catalyst and solvent water, performing a stirring reaction at 25-60 DEG C for 4-8 hours, performing TLC (thin-layer chromatography) monitoring till the arylboronic acid (1) is completely converted, replacing air in the reaction system by using N2, adding a terminal alkyne (2), performing a reaction at 40-80 DEG C for 6-10 hours under the protection of N2, and performing post-treatment on the reaction solution to obtain a product (II). By adopting the preparation method, Cu-coated SBA-15-PTAA is used as a catalyst, a series of 1-aryl-4-substituted-1,2,3-triazole compounds are prepared through a one-pot Chan-Lam/Click series method without additionally adding a reducing agent, the developed catalytic method is green, safe and economical, the amount of three wastes (wastegas, waste water and industrial residue) is small, the yield of a target product is high, and the substrate application range is wide.
Copper-γ-cyclodextrin complexes immobilized on hexagonal boron nitride as an efficient catalyst in the multicomponent synthesis of 1,2,3-triazoles
Nie, Ruifang,Sang, Rui,Ma, Xiaojun,Zheng, Yang,Cheng, Xu,Li, Weijian,Guo, Li,Jin, Hui,Wu, Yong
, p. 286 - 292 (2016/10/30)
A copper-γ-cyclodextrin complex immobilized on hexagonal boron nitride (h-BN@γ-CD@Cu(OAc)2) has been prepared for the first time. This recoverable and reusable heterogeneous catalyst can be used in the click synthesis of 1,2,3-triazoles via a one-pot three-component reaction of boracic acid, terminal alkynes, and sodium azide at room temperature in water. FT-IR, XRD, SEM, XPS, TG, and ICP-AES techniques were used to characterize the catalyst. In general, this reaction, with the aid of this new catalyst, afforded the corresponding products with good yields and excellent tolerance of the functional groups.
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
supporting information, p. 17635 - 17639 (2015/02/05)
A novel synthetic approach toward 1,4-disubstitut-ed 1,2,3-triazoles by C-N- and N-N-bond formation has been established under transition-metal-free conditions. Complete control of the regioselectivity was successfully achieved. Commercially available ani
I2/TBPB mediated oxidative reaction of N-tosylhydrazones with anilines: Practical construction of 1,4-disubstituted 1,2,3-triazoles under metal-free and azide-free conditions
Cai, Zhong-Jian,Lu, Xin-Mou,Zi, You,Yang, Chao,Shen, Ling-Jie,Li, Jian,Wang, Shun-Yi,Ji, Shun-Jun
, p. 5108 - 5111 (2014/12/11)
An efficient I2 (20 mol %)/TBPB mediated oxidative formal [4 + 1] cycloaddition of N-tosylhydrazones with anilines via C-N/N-N bond formation and S-N cleavage has been developed. This protocol represents a simple, general, and efficient approac
Copper(I) heteroleptic bis(NHC) and mixed NHC/phosphine complexes: Syntheses and catalytic activities in the one-pot sequential CuAAC reaction of aromatic amines
Guo, Shuai,Lim, Miao Hui,Huynh, Han Vinh
, p. 7225 - 7233 (2014/01/06)
A series of 2-coordinate heteroleptic Cu(I) complexes of the general formula [Cu(IPr)(L)]PF6 (2-5, L = NHC or phosphine) have been synthesized via either (i) chlorido substitution by phosphine or in situ generated free NHC or (ii) the Ag-NHC transfer protocol using [CuCl(IPr)] (1) as a precursor (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene). The reactions of precursor 1 with diphosphine ligands afforded 3-coordinate heteroleptic Cu(I) complexes of the type [Cu(IPr)(L2)]PF6 (6 and 7, L2 = diphosphine). Complexes 1-7 have been subjected to a catalytic one-pot sequential CuAAC study, in which aromatic amines serve as the precursors to aryl azides. Hetero-bis(NHC) complexes 2-4 proved to be generally superior compared to their mixed NHC/phosphine counterparts 5-7. Overall, complex [Cu(Bn2-imy)(IPr)]PF6 (2), bearing the Bn 2-imy (Bn2-imy = 1,3-dibenzyl-imidazolin-2-ylidene) coligand, showed the best catalytic performance.
Copper-mediated synthesis of 1,2,3-triazoles from N-tosylhydrazones and anilines
Chen, Zhengkai,Yan, Qiangqiang,Liu, Zhanxiang,Xu, Yiming,Zhang, Yuhong
, p. 13324 - 13328 (2014/01/06)
NNNifty targets: In a straightforward copper-mediated synthesis of 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles, readily available aniline and N-tosylhydrazone substrates underwent cyclization through Ci￡N and Ni￡N bond formation (see scheme
Magnetically recoverable CuFe2O4 nanoparticles: Catalyzed synthesis of aryl azides and 1,4-diaryl-1,2,3-triazoles from boronic acids in water
Kumar, A. Suresh,Reddy, M. Amarnath,Knorn,Reiser,Sreedhar
, p. 4674 - 4680 (2013/07/26)
Magnetically recoverable and reusable CuFe2O4 nanoparticles are shown to be highly efficient catalysts for the one-pot synthesis of biologically important 1,4-diaryl-1,2,3-triazoles starting from boronic acids, sodium azide, and acetylenes. The use of aqueous reaction medium at room temperature, the low cost and facile recovery of the catalyst by application of an external magnetic field, and consistently high catalytic efficiency for at least three consecutive cycles renders the protocol operationally attractive. Magnetic and catalytically competent CuFe 2O4 nanoparticles proved to be highly efficient in the three-component synthesis of 1,4-diaryl-1,2,3-triazoles, a class of compounds that has been recognized for its anticancer activity. Copyright
One-pot, three-component copper-catalysed 'click' triazole synthesis utilising the inexpensive, shelf-stable diazotransfer reagent imidazole-1-sulfonyl azide hydrochloride
Smith, Neal M.,Greaves, Michelle J.,Jewell, Robert,Perry, Matthew W. D.,Stocks, Michael J.,Stonehouse, Jeffrey P.
scheme or table, p. 1391 - 1394 (2009/10/16)
A practical and efficient one-pot procedure for the regioselective synthesis of functionalised 1,4-disubstituted 1,2,3-triazoles from primary amines and terminal acetylenes has been established utilising the inexpensive, shelf-stable diazotransfer reagent
