Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction
- Corresponding author: Ma Hai-Yan, haiyanma@ecust.edu.cn Xing Chun-Hui, xingch@sioc.ac.cn
Citation: Liu Xiao-Dong, Ma Hai-Yan, Xing Chun-Hui, Lu Long. Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction[J]. Chinese Chemical Letters, ;2017, 28(8): 1780-1783. doi: 10.1016/j.cclet.2017.03.031
A. Padwa, W.H. Pearson, Synthetic Applications Of 1, 3-Dipolar Cycloaddition Chemistry Toward Heterocycles And Natural Products, Wiley, New York, 2002.
(a) Y. Al-Abed, D. Dabideen, B. Aljabari, et al. , ISO-1 binding to the tautomerase active site of MIF inhibits its pro-inflammatory activity and increases survival in severe sepsis, J. Biol. Chem. 280(2005) 36541-36544;
(b) M. C. Pirrung, L. N. Tumey, C. R. H. Raetz, et al. , Inhibition of the antibacterial target UDP-(3-O-αcyl)-N-acetylglucosamine deacetylase (LpxC): Isoxazoline Zinc amidase inhibitors bearing diverse metal binding groups, J. Med. Chem. 45(2002) 4359-4370;
(c) J. B. Lubetsky, A. Dios, J. Han, et al. , The tautomerase active site of macrophage migration inhibitory factor is a potential target for discovery of novel anti-inflammatory agents, J. Biol. Chem. 277(2002) 24976-24982;
(d) M. L. Quan, C. D. Ellis, A. Y. Liauw, et al. , Design and synthesis of isoxazoline derivatives as factor Xa inhibitors 2, J. Med. Chem. 42(1999) 2760-2773.
Kawai H., Sugita Y., Tokunaga E.. Diastereoselective additive trifluoromethylation/halogenation of isoxazole triflones:Synthesis of allcarbon-functionalized trifluoromethyl isoxazoline triflones[J]. Chem. Open, 2014,3:14-18.
(a) M. Gucma, W. M. Gołębiewski, 1, 3-Dipolar cycloaddition reaction of nitrile oxides revisited-Unusual side products characterized by 2D NMR, J. Heterocycl. Chem. 51(2014) 572-578;
(b) H. Suga, Y. Adachi, K. Fujimoto, et al. , Asymmetric 1, 3-dipolar cycloaddition reactions of nitrile oxides catalyzed by chiral binaphthyldiimine-Ni(Ⅱ) complexes, J. Org. Chem. 74(2009) 1099-1113;
(c) Y. Brinkmann, R. J. Madhushaw, R. Jazzar, G. Bernardinellib, E. P. Kündig, Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions, Tetrahedron 63(2007) 8413-8419;
(d) A. Ros, E. Alvarez, H. Dietrich, R. Fernández, J. M. Lassaletta, A practical synthesis of enantiopure 4, 5-dihydroisoxazole-5-carboxylic acids, Synlett (2005) 2899-2904;
(e) M. P. Sibi, K. Itoh, C. P. Jasperse, Chiral Lewis acid catalysis in nitrile oxide cycloadditions, J. Am. Chem. Soc. 126(2004) 5366-5367;
(f) C. D. Davies, S. P. Marsden, E. S. E. Stokes, Enhanced asymmetric induction in cycloadditions to bridgehead-chiral vinyl dioxazaborocines, Tetrahedron Lett. 41(2000) 4229-4233.
(a) Q. Wei, J. R. Chen, X. Q. Hu, et al. , Photocatalytic radical trifluoromethylation/cyclization cascade: synthesis of CF3-containing pyrazolines and isoxazolines, Org. Lett. 17(2015) 4464-4467;
(b) H. Kawai, S. Okusu, E. Tokunaga, N. Shibata, Enantioselective synthesis of 5-trifluoromethyl -2-isoxazolines and their N-oxides by[Hydroxy(tosyloxy) iodo]benzene-mediated oxidative N-O coupling, Eur. J. Org. Chem. (2013) 6506-6509;
(c) Y. T. He, L. H. Li, Y. F. Yang, et al. , Copper-catalyzed synthesis of trifluoromethyl-substituted isoxazolines, Chem. Commun. 49(2013) 5687-5689;
(d) R. Aggarwal, A. Bansal, A. Mittal, Synthesis and antimicrobial activity of 3-(2-thienyl)-4-arylazo-5-hydroxy-5-trifluoromethyl-D2-isoxazolines and 3-(2-thienyl)-4-arylazo-5-trifluoromethylisoxazoles, J. Fluor. Chem. 145(2013) 95-101;
(e) A. L. Norman, M. D. Mosher, Enantioselectivity in the synthesis of 3, 5-disubstituted △2-isoxazolines, Tetrahedron Lett. 49(2008) 4153-4155;
(f) V. Kumar, R. Aggarwal, S. P. Singh, The reaction of hydroxylamine with aryl trifluoromethyl-b-diketones: synthesis of 5-hydroxy-5-trifluoromethyl-△2-isoxazolinesandtheirdehydration to 5-trifluoromethylisoxazoles, J. Fluor. Chem. 127(2006) 880-888;
(g) M. Zielinska-Błajet, R. Kowalczyk, J. Skarzewski, Ring-closure reactions _through intramolecular substitution of thiophenoxide by oxygen and nitrogen nucleophiles: simple stereospecific synthesis of 4, 5-dihydroisoxazoles and 4, 5-dihydropyrazoles, Tetrahedron 61(2005) 5235-5240;
(h) J. Diab, A. Laurent, I. L. Dréan, Synthesis of isomeric trifluoromethyl pyrazoles and isoxazoles, J. Fluor. Chem. 84(1997) 145-147.
Ozoe Y., Asahi M., Ozoe F., Nakahira K., Mita T.. The antiparasitic isoxazoline A1443 is a potent blocker of insect ligand-gated chloride channels[J]. Biochem. Biophys. Res. Commun., 2010,391:744-749. doi: 10.1016/j.bbrc.2009.11.131
(a) H. Kawai, N. Shibata, Asymmetric synthesis of agrochemically attractive trifluoromethylated dihydroazoles and related compounds under organocatalysis, Chem. Rec. 14(2014) 1024-1040;
(b) K. Matoba, H. Kawai, T. Furukawa, et al. , Enantioselective synthesis of trifluoromethyl-substituted 2-isoxazolines: asymmetric hydroxylamine/enone cascade reaction, Angew. Chem. Int. Ed. 49(2010) 5762-5766;
(c) A. Pohjakallio, P. M. Pihko, Enantioselective synthesis of 2-isoxazolines by a one-flask conjugate addition/oxime-transfer process, Chem. Eur. J. 15(2009) 3960-3964.
(a) P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Second Edition, Wiley-VCH GmbH & Co: KGaA, 2013;
(b) K. Uneyama, Organofluorine chemistry, Wiley-Blackwell, Oxford, 2006;
(c) R. Filler, Y. Kobayashi, L. M. Yagupolskii, Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993.
(a) V. M. Muzalevskiy, A. V. Shastin, E. S. Balenkova, G. Haufe, V. G. Nenajdenko, Synthesis of trifluoromethyl pyrroles and their benzo analogues, Synthesis (2009) 3905-3929;
(b) A. W. Erian, Recent trends in the chemistry of fluorinated five and sixmembered heterocycles, J. Heterocycl. Chem. 38(2001) 793-808;
(c) J. T. Welch, Advances in the preparation of biologically active organofluorine compounds, Tetrahedron 43(1987) 3123-3197.
(a) A. Reichelt, S. F. Martin, Synthesis and properties of cyclopropane-derived peptidomimetics, Acc. Chem. Res. 39(2006) 433-442;
(b) H. Lebel, J. F. Marcoux, C. Molinaro, A. B. Charette, Stereoselective cyclopropanation reactions, Chem. Rev. 103(2003) 977-1050;
(c) W. A. Donaldson, Synthesis of cyclopropane containing natural products, Tetrahedron 57(2001) 8589-8627.
Wang Y., Yuan Y., Xing C.H., Lu L.. Trifluoromethanesulfonic acid-catalyzed solvent-free bisindolylation of trifluoromethyl ketones[J]. Tetrahedron Lett., 2014,55:1045-1048. doi: 10.1016/j.tetlet.2013.12.078
Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
Guihuang Fang , Wei Chen , Hongwei Yang , Haisheng Fang , Chuang Yu , Maoxiang Wu . Improved performance of LiMn0.8Fe0.2PO4 by addition of fluoroethylene carbonate electrolyte additive. Chinese Chemical Letters, 2024, 35(6): 108799-. doi: 10.1016/j.cclet.2023.108799
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
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423
Xiao Li , Wanqiang Yu , Yujie Wang , Ruiying Liu , Qingquan Yu , Riming Hu , Xuchuan Jiang , Qingsheng Gao , Hong Liu , Jiayuan Yu , Weijia Zhou . Metal-encapsulated nitrogen-doped carbon nanotube arrays electrode for enhancing sulfion oxidation reaction and hydrogen evolution reaction by regulating of intermediate adsorption. Chinese Chemical Letters, 2024, 35(8): 109166-. doi: 10.1016/j.cclet.2023.109166
Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO2 nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108
Guan-Nan Xing , Di-Ye Wei , Hua Zhang , Zhong-Qun Tian , Jian-Feng Li . Pd-based nanocatalysts for oxygen reduction reaction: Preparation, performance, and in-situ characterization. Chinese Journal of Structural Chemistry, 2023, 42(11): 100021-100021. doi: 10.1016/j.cjsc.2023.100021
Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
Tengjia Ni , Xianbiao Hou , Huanlei Wang , Lei Chu , Shuixing Dai , Minghua Huang . Controllable defect engineering based on cobalt metal-organic framework for boosting oxygen evolution reaction. Chinese Journal of Structural Chemistry, 2024, 43(1): 100210-100210. doi: 10.1016/j.cjsc.2023.100210