Citation:
Fen Zhao, Zhen Chen, Kai Xie, Rui Yang, Yu-Bo Jiang. One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes[J]. Chinese Chemical Letters,
;2016, 27(01): 109-113.
doi:
10.1016/j.cclet.2015.09.021
-
A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.
-
-
-
[1]
[1](a) D.J. Lee, E.J. Yoo, Efficient synthesis of C-N-coupled heterobiaryls by sequential N-H functionalization reactions, Org. Lett. 17(2015) 1830-1833;(b) T. Ryu, Y. Baek, P.H.J. Lee, Synthesis of pyrazines from rhodium-catalyzed reaction of 2H-azirines with N-sulfonyl 1,2,3-triazoles, J. Org. Chem. 80(2015) 2376-2383;(c) S. Shi, C. Kuang, Palladium-catalyzed ortho-alkoxylation of 2-aryl-1,2,3-triazoles, J. Org. Chem. 79(2014) 6105-6112.
-
[2]
[2](a) C. Testa, M. Scrima, M. Grimaldi, et al., 1,4-Disubstituted-[1,2,3] triazolylcontaining analogues of MT-Ⅱ:design, synthesis, conformational analysis, and biological activity, J. Med. Chem. 57(2014) 9424-9434;(b) P. Thirumurugan, D. Matosiuk, K. Jozwiak, Click chemistry for drug development and diverse chemical-biology applications, Chem. Rev. 113(2013) 4905-4979.
-
[3]
[3](a) S.G. Agalave, S.R. Maujan, V.S. Pore, Click chemistry:1,2,3-triazoles as pharmacophores, Chem. Asian J. 6(2011) 2696-2718;(b) R.W. Robey, A.R. Chakraborty, A. Basseville, et al., Histone deacetylase inhibitors:emerging mechanisms of resistance, Mol. Pharm. 8(2011) 2021-2031;(c) C. Sheng, W. Zhang, New lead structures in antifungal drug discovery, Curr. Med. Chem. 18(2011) 733-766.
-
[4]
[4](a) T. Muller, S. Brase, Click chemistry finds its way into covalent porous organic materials, Angew. Chem. Int. Ed. 50(2011) 11844-11845;(b) Y.H. Lau, P.J. Rutledge, M. Watkinson, et al., Chemical sensors that incorporate click-derived triazoles, Chem. Soc. Rev. 40(2011) 2848-2866;(c) C. Chu, R. Liu, Application of click chemistry on preparation of separation materials for liquid chromatography, Chem. Soc. Rev. 40(2011) 2177-2188.
-
[5]
[5] U.F. Rö hrig, S.R. Majjigapu, A. Grosdidier, et al., Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition, J. Med. Chem. 55(2012) 5270-5290.
-
[6]
[6] M.A. Totir, P.S. Padayatti, M.S. Helfand, et al., Effect of the inhibitor-resistant M69V substitution on the structures and populations of trans-enamine(-lactamase intermediates), Biochemistry 45(2006) 11895-11904.
-
[7]
[7] J. Bian, L. Zhang, Y. Han, C. Wang, L. Zhang, Histone deacetylase inhibitors:potent anti-leukemic agents, Curr. Med. Chem. 22(2015) 2065-2074.
-
[8]
[8] K.E. Akri, K. Bougrin, J. Balzarini, A. Faraj, R. Benhida, Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides, Bioorg. Med. Chem. Lett. 17(2007) 6656-6659.
-
[9]
[9] R. Huisgen, Centenary lecture. 1,3-Dipolar cycloadditions, Proc. Chem. Soc.(1961) 357-369.
-
[10]
[10] V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, A stepwise huisgen cycloaddition process:copper(I)-catalyzed regioselective ligation of azides and terminal alkynes, Angew. Chem. Int. Ed. 41(2002) 2596-2599.
-
[11]
[11](a) X.J. Quan, Z.H. Ren, Y.Y. Wang, Z.H. Guan, p-Toluenesulfonic acid mediated 1,3-dipolar cycloaddition of nitroolefins with NaN3 for synthesis of 4-aryl-NH-1,2,3-triazoles, Org. Lett. 16(2014) 5728-5731;(b) A. Bolje, D. Urankar, J. Kosmrlj, Synthesis and NMR analysis of 1,4-disubstituted 1,2,3-triazoles tethered to pyridine, pyrimidine, and pyrazine rings, Eur. J. Org. Chem. 36(2014) 8167-8181.
-
[12]
[12] T.R. Chan, R. Hilgraf, K.B. Sharpless, V.V. Fokin, Polytriazoles as copper(I)-stabilizing ligands in catalysis, Org. Lett. 6(2004) 2853-2855.
-
[13]
[13] H.A. Orgueira, D. Fokas, Y. Isome, et al., Regioselective synthesis of[1,2,3]-triazoles catalyzed by Cu(I) generated in situ from Cu(0) nanosize activated powder and amine hydrochloride salts, Tetrahedron Lett. 46(2005) 2911-2914.
-
[14]
[14](a) D. Wang, L. Etienne, M. Echeverria, S. Moya, D. Astruc, A highly active and magnetically recoverable tris(triazolyl)-CuI catalyst for alkyne-azide cycloaddition reactions, Chem. Eur. J. 20(2014) 4047-4054;(b) A. Pathigoolla, R.P. Pola, K.M. Sureshan, A versatile solvent-free azide-alkyne click reaction catalyzed by in situ generated copper nanoparticles, Appl. Catal. A Gen. 453(2013) 151-158.
-
[15]
[15] D.B. Ramachary, A.B. Shashank, S. Karthik, An organocatalytic azide-aldehyde[3+2] cycloaddition:high-yielding regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles, Angew. Chem. Int. Ed. 53(2014) 10420-10424.
-
[16]
[16](a) Y. Jiang, C. Kuang, Q. Yang, The use of calcium carbide in the synthesis of 1-monosubstituted aryl 1,2,3-triazole via click chemistry, Synlett 19(2009) 3163-3166;(b) L. Tao, L.L. Zhang, S.J. Shen, X.P. Hang, Microwave-promoted rapid synthesis of 1-aryl-1,2,3-triazoles, Chin. Chem. Lett. 12(2001) 763-764.
-
[17]
[17](a) Y. He, E. Sun, Y. Zhao, L. Hai, Y. Wu, The one-pot synthesis of 4-aryl-1H-1,2,3-triazoles without azides and metal catalization, Tetrahedron Lett. 55(2014) 111-115;(b) X. Wang, C. Kuang, Q. Yang, Copper-catalyzed synthesis of 4-aryl-1H-1,2,3-triazoles from 1,1-dibromoalkenes and sodium azide, Eur. J. Org. Chem. 2(2012) 424-428.
-
[18]
[18](a) S.W. Kwok, J.R. Fotsing, R.J. Fraser, V.O. Rodionov, V.V. Fokin, Transitionmetal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles, Org. Lett. 12(2010) 4217-4219;(b) X.Z. Cheng, W. Liu, Z.D. Huang, Sodium hydride-mediated synthesis of 1,5-diaryl-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and organic azides, Chin. Chem. Lett. 24(2013) 764-766.
-
[19]
[19](a) G.C. Davir, S.I. Itzel, G.G. Carlos, et al., A novel and facile synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from benzylic alcohols through a one-pot, threecomponent system, Tetrahedron Lett. 56(2015) 514-516;(b) Z.G. Luo, Y. Zhao, F. Xu, et al., Synthesis and thermal properties of novel calix[4] arene derivatives containing 1,2,3-triazole moiety via K2CO3-catalyzed 1,3-dipolar cycloaddition reaction, Chin. Chem. Lett. 25(2014) 1346-1348.
-
[20]
[20] A. Zarei, One-pot, efficient, and regioselective syntheses of 1,4-disubstituted 1,2,3-triazoles using aryldiazonium silica sulfates in water, Tetrahedron Lett. 53(2012) 5176-5179.
-
[21]
[21] B.S.P.A. Kumar, K.H.V. Reddy, K. Karnakar, et al., Copper on chitosan:an efficient and easily recoverable heterogeneous catalyst for one pot synthesis of 1,2,3-triazoles from aryl boronic acids in water at room temperature, Tetrahedron Lett. 56(2015) 1968-1972.
-
[22]
[22] Y. Chen, Z.J. Zhuo, D.M. Cui, C. Zhang, Copper catalyzed synthesis of 1-aryl-1,2,3-triazoles from aryl iodides, alkynes, and sodium azide, J. Organomet. Chem. 749(2014) 215-218.
-
[23]
[23] S. Guo, M.H. Lim, H.V. Huynh, Copper(I) heteroleptic bis(NHC) and mixed NHC/phosphine complexes:syntheses and catalytic activities in the one-pot sequential CuAAC reaction of aromatic amines, Organometallics 32(2013) 7225-7233.
-
[24]
[24] F. Zhao,Z. Chen, P. Lei, L. Kong, Y. Jiang, Facile one-pot synthesis ofaryl azides from nitrobenzenes, Tetrahedron Lett. 56(2015) 2197-2199.
-
[1]
-
-
-
[1]
Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
-
[2]
Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994
-
[3]
Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
-
[4]
Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
-
[5]
Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A2-A1-D-A1-A2 type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
-
[6]
Lanfang Wang , Jiangnan Lv , Yujia Li , Yanqing Hao , Wenjiao Liu , Hui Zhang , Xiaohong Xu . One-step synthesis of nanowoven ball-like NiS-WS2 for high-efficiency hydrogen evolution. Chinese Chemical Letters, 2025, 36(1): 109597-. doi: 10.1016/j.cclet.2024.109597
-
[7]
Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
-
[8]
Tao Ban , Xi-Yang Yu , Hai-Kuo Tian , Zheng-Qing Huang , Chun-Ran Chang . One-step conversion of methane and formaldehyde to ethanol over SA-FLP dual-active-site catalysts: A DFT study. Chinese Chemical Letters, 2024, 35(4): 108549-. doi: 10.1016/j.cclet.2023.108549
-
[9]
Xingqun Pu , Rongrong Liu , Yuting Xie , Chenjing Yang , Jingyi Chen , Baoling Guo , Chun-Xia Zhao , Peng Zhao , Jian Ruan , Fangfu Ye , David A Weitz , Dong Chen . One-step preparation of biocompatible amphiphilic dimer nanoparticles with tunable particle morphology and surface property for interface stabilization and drug delivery. Chinese Chemical Letters, 2025, 36(3): 109820-. doi: 10.1016/j.cclet.2024.109820
-
[10]
Tao Tang , Chen Li , Sipu Li , Zhong Qiu , Tianqi Yang , Beirong Ye , Shaojun Shi , Chunyang Wu , Feng Cao , Xinhui Xia , Minghua Chen , Xinqi Liang , Xinping He , Xin Liu , Yongqi Zhang . One-step constructing advanced N-doped carbon@metal nitride as ultra-stable electrocatalysts via urea plasma under room temperature. Chinese Chemical Letters, 2024, 35(11): 109887-. doi: 10.1016/j.cclet.2024.109887
-
[11]
Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
-
[12]
Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
-
[13]
Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
-
[14]
Qi Li , Zi-Lu Wang , Yun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991
-
[15]
Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
-
[16]
Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
-
[17]
Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
-
[18]
Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
-
[19]
Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
-
[20]
Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(756)
- HTML views(33)