Citation: Hou Jiao, Zhang Xinting, Yu Wenquan, Chang Junbiao. I2-Mediated Oxidative C-O Bond Formation for the Synthesis of Isoxazoles[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3236-3241. doi: 10.6023/cjoc201806026 shu

I2-Mediated Oxidative C-O Bond Formation for the Synthesis of Isoxazoles

  • Corresponding author: Yu Wenquan, wenquan_yu@zzu.edu.cn Chang Junbiao, changjunbiao@zzu.edu.cn
  • Received Date: 16 June 2018
    Revised Date: 2 August 2018
    Available Online: 23 December 2018

    Fund Project: the Outstanding Young Talent Research Fund of Zhengzhou University 1521316004the National Natural Science Foundation of China 81773570Project supported by the National Natural Science Foundation of China (Nos. 81773570, 81330075) and the Outstanding Young Talent Research Fund of Zhengzhou University (No. 1521316004)the National Natural Science Foundation of China 81330075

Figures(1)

  • A variety of mono-, di-, and tri-substituted (aryl, alkyl, and/or alkenyl) isoxazoles were synthesized from readily accessible α, β-unsaturated oximes via I2-mediated oxidative C-O bond formation. The features of this synthetic approach include no use of transition metals, simple operation, mild reaction conditions, short reaction time, and broad substrate scope.
  • 加载中
    1. [1]

      (a) Grünanger, P.; Vita-Finzi, P.; Dowling, J. E. In Chemistry of Heterocyclic Compounds: Isoxazoles, Part 2, Vol. 49, Eds.: Taylor, E. C.; Wipf, P., John Wiley & Sons, New York, 1999, pp. 1~888.
      (b) Vitale, P.; Scilimati, A. Curr. Org. Chem. 2013, 17, 1986.
      (c) Vitale, P.; Scilimati, A. Synthesis 2013, 45, 2940.
      (d) Hu, F.; Szostak, M. Adv. Synth. Catal. 2015, 357, 2583.

    2. [2]

      (a) Mares, D.; Romagnoli, C.; Tosi, B.; Benvegnu, R.; Bruni, A.; Vicentini, C. B. Fungal Genet. Biol. 2002, 36, 47.
      (b) Ohigashi, A.; Kanda, A.; Tsuboi, H.; Hashimoto, N. Org. Process Res. Dev. 2005, 9, 179.
      (c) Yu, G. J.; Iwamoto, S.; Robins, L. I.; Fettinger, J. C.; Sparks, T. C.; Lorsbach, B. A.; Kurth, M. J. J. Agric. Food Chem. 2009, 57, 7422.

    3. [3]

      (a) Baraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simoni, D. Synthesis 1987, 857.
      (b) Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D. R.; Myers, A. G. Science 2005, 308, 395.
      (c) Ikeda, R.; Kuwano, R. Chem.-Eur. J. 2016, 22, 8610.

    4. [4]

      (a) Ahmed, M. S. M.; Kobayashi, K.; Mori, A. Org. Lett. 2005, 7, 4487.
      (b) Tang, S.; He, J.; Sun, Y.; He, L.; She, X. Org. Lett. 2009, 11, 3982.
      (c) Dou, G.; Xu, P.; Li, Q.; Xi, Y.; Huang, Z.; Shi, D. Molecules 2013, 18, 13645.
      (d) Gao, P.; Li, H.-X.; Hao, X.-H.; Jin, D.-P.; Chen, D.-Q.; Yan, X.-B.; Wu, X.-X.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2014, 16, 6298.
      (e) Harigae, R.; Moriyama, K.; Togo, H. J. Org. Chem. 2014, 79, 2049.
      (f) Kivrak, A.; Zora, M. Tetrahedron 2014, 70, 817.
      (g) Raghava, B.; Parameshwarappa, G.; Acharya, A.; Swaroop, T. R.; Rangappa, K. S.; Ila, H. Eur. J. Org. Chem. 2014, 1882.
      (h) Chen, W.; Zhang, J.; Wang, B.; Zhao, Z.; Wang, X.; Hu, Y. J. Org. Chem. 2015, 80, 2413.
      (i) He, Y.; Xie, Y.-Y.; Wang, Y.-C.; Bin, X.-M.; Hu, D.-C.; Wang, H.-S.; Pan, Y.-M. RSC Adv. 2016, 6, 58988.
      (j) Kumar, G. R.; Kumar, Y. K.; Reddy, M. S. Chem. Commun. 2016, 52, 6589.

    5. [5]

      (a) Sun, Y.; Abdukader, A.; Zhang, H.; Yang, W.; Liu, C. RSC Adv. 2017, 7, 55786.
      (b) Abdukader, A.; Sunb, Y.; Zhang, Z.; Liu, C. Catal. Commun. 2018, 105, 43.
      (c) Desai, V. G.; Naik, S. R.; Dhumaskar, K. L. Synth. Commun. 2014, 44, 1453.
      (d) Kurangi, R. F.; Kawthankar, R.; Sawal, S.; Desai, V. G.; Tilve, S. G. Synth. Commun. 2007, 37, 587.
      (e) Desai, V. G.; Tilve, S. G. Synth. Commun. 1999, 29, 3017.
      (f) Wei, X.; Fang, J.; Hu, Y.; Hu, H. Synthesis 1992, 1205.
      (g) Sharma, T. C.; Rojindar, S.; Berge, D. D.; Kale, A. V. Indian J. Chem. 1986, 25B, 437.

    6. [6]

      (a) Zi, W.; Zuo, Z.; Ma, D. Acc. Chem. Res. 2015, 48, 702.
      (b) Zhao, J.; Gao, W.; Chang, H.; Li, X.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 1941(in Chinese).

    7. [7]

      (a) Uyanik, M.; Okamoto, H.; Yasui, T.; Ishihara, K. Science 2010, 328, 1376.
      (b) Finkbeiner, P.; Nachtsheim, B. J. Synthesis 2013, 45, 979.
      (c) Liu, D.; Lei, A. Chem. Asian J. 2015, 10, 806.
      (d) Satish, G. Synlett 2015, 26, 1913.
      (e) Gao, W.-C.; Hu, F.; Huo, Y.-M.; Chang, H.-H.; Li, X.; Wei, W.-L. Org. Lett. 2015, 17, 3914.

    8. [8]

      Gao, W.-C.; Wang, R.-L.; Zhang, C. Org. Biomol. Chem. 2013, 11, 7123.  doi: 10.1039/c3ob41566j

    9. [9]

      Rong, H.-J.; Yao, J.-J.; Li, J.-K.; Qu, J. J. Org. Chem. 2017, 82, 5557.  doi: 10.1021/acs.joc.7b00361

    10. [10]

      (a) Yu, W.; Huang, G.; Zhang, Y.; Liu, H.; Dong, L.; Yu, X.; Li, Y.; Chang, J. J. Org. Chem. 2013, 78, 10337.
      (b) Niu, P.; Kang, J.; Tian, X.; Song, L.; Liu, H.; Wu, J.; Yu, W.; Chang, J. J. Org. Chem. 2015, 80, 1018.
      (c) Yu, W.; Chang, J. Chin. J. Org. Chem. 2018, 38, 215(in Chinese).

    11. [11]

      Through a systematic literature search, some examples of 3-methyl isoxazole synthesis using I2/KI in THF/H2O were found in the following references: (a) Büchi, G.; Vederas, J. C. J. Am. Chem. Soc. 1972, 94, 9128.
      (b) Alberola, A.; Bañez, J. M.; Calvo, L.; Rodríguez, M. T. R.; Sañudo, M. C. J. Heterocycl. Chem. 1993, 30, 467.

    12. [12]

      Zhu, Y.-P.; Fei, Z.; Liu, M.-C.; Jia, F.-C.; Wu, A.-X. Org. Lett. 2013, 15, 378.  doi: 10.1021/ol303331g

    13. [13]

      Zhang, X.; Kang, J.; Niu, P.; Wu, J.; Yu, W.; Chang, J. J. Org. Chem. 2014, 79, 10170.  doi: 10.1021/jo501844x

    14. [14]

      Isoxazoline intermediate 3a was obtained according to the procedure described in reference 11b.

    15. [15]

      Barluenga, J.; Jardon, J.; Rubio, V.; Gotor, V. J. Org. Chem. 1983, 48, 1379.

    16. [16]

      Kidwai, M.; Kukreja, S.; Thakur, R. Lett. Org. Chem. 2006, 3, 135.

    17. [17]

      Barnes, R. P.; Dodson, L. B. J. Am. Chem. Soc. 1943, 65, 1585.  doi: 10.1021/ja01248a039

    18. [18]

      Rao, K. S. R. K. M.; Rao, N. V. S. Indian J. Chem. 1968, 6, 66.

    19. [19]

      Morrocchi, S.; Ricca, A.; Zanarotti, A.; Bianchi, G.; Gandolfi, R.; Grünanger, P. Tetrahedron Lett. 1969, 10, 3329.

    20. [20]

      Mitchell, A. D.; Nonhebel, D. C. Tetrahedron 1976, 32, 2437.  doi: 10.1016/0040-4020(76)87030-5

    21. [21]

      Bianchi, G. Tetrahedron 1965, 21, 817.  doi: 10.1016/0040-4020(65)80014-X

  • 加载中
    1. [1]

      Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)3I3]- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458

    2. [2]

      Pengcheng Su , Shizheng Chen , Zhihong Yang , Ningning Zhong , Chenzi Jiang , Wanbin Li . Vapor-phase postsynthetic amination of hypercrosslinked polymers for efficient iodine capture. Chinese Chemical Letters, 2024, 35(9): 109357-. doi: 10.1016/j.cclet.2023.109357

    3. [3]

      Junyou Ding , Xiaotong Li , Hongmin Lin , Bochao Ye , Xing Zhou , Feihu Cui , Yingming Pan , Haitao Tang . Highly regioselective hydrogermylation of unsaturated C-C bonds over ligand-control single atom palladium catalysts. Chinese Chemical Letters, 2025, 36(11): 111286-. doi: 10.1016/j.cclet.2025.111286

    4. [4]

      Jinyuan Cui ,  Tingting Yang ,  Teng Xu ,  Jin Lin ,  Kunlong Liu ,  Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438

    5. [5]

      Yajun Hou , Chuanzheng Zhu , Qiang Wang , Xiaomeng Zhao , Kun Luo , Zongshuai Gong , Zhihao Yuan . ~2.5 nm pores in carbon-based cathode promise better zinc-iodine batteries. Chinese Chemical Letters, 2024, 35(5): 108697-. doi: 10.1016/j.cclet.2023.108697

    6. [6]

      Xinyi Cao , Yucheng Jin , Hailong Wang , Xu Ding , Xiaolin Liu , Baoqiu Yu , Xiaoning Zhan , Jianzhuang Jiang . A tetraaldehyde-derived porous organic cage and covalent organic frameworks: Syntheses, structures, and iodine vapor capture. Chinese Chemical Letters, 2024, 35(9): 109201-. doi: 10.1016/j.cclet.2023.109201

    7. [7]

      Dongying Fu , Lin Pan , Yanli Ma , Yue Zhang . Bilayered Dion–Jacobson lead-iodine hybrid perovskite with aromatic spacer for broadband photodetection. Chinese Chemical Letters, 2025, 36(2): 109621-. doi: 10.1016/j.cclet.2024.109621

    8. [8]

      Muhammad Riaz ,  Rakesh Kumar Gupta ,  Di Sun ,  Mohammad Azam ,  Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427

    9. [9]

      Xiang Li , Beibei Zhang , Zhixiang Wang , Xiangyu Chen . Organocatalyzed iodine-mediated reversible-deactivation radical polymerization via photoinduced charge transfer complex catalysis. Chinese Chemical Letters, 2025, 36(6): 110383-. doi: 10.1016/j.cclet.2024.110383

    10. [10]

      Ming-Chang Wang , Zhi Lin , Jia-Jia Li , Jia-Min Lian , Yun-Xia Hu , Yan Chen , Ke-Zhao Du , Jin Chen . Bromine for iodine: Unlocking short-wavelength UV phase matching in nonlinear optical metal halides. Chinese Chemical Letters, 2026, 37(10): 111639-. doi: 10.1016/j.cclet.2025.111639

    11. [11]

      Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024

    12. [12]

      Ting Zhang , Jia Chen , Mingxia Sun , Juanjuan Wang , Lulu Wang , Shuzhe Guan , Hongdeng Qiu . Bis-trimethylammonium pillar[5]arene and biphenyldisulfonic acid-based ionic pair assembled single crystals for iodine adsorption. Chinese Chemical Letters, 2026, 37(5): 111790-. doi: 10.1016/j.cclet.2025.111790

    13. [13]

      Guolong Lu , Jingwen Zhang , Zhiwei Wang , Zhigui Wang , Yanhong Feng , Cejun Hu , Longchao Zhuo , Xijun Liu . Sulfur vacancy-rich MoS2 anchored oxidized graphene as advanced catalysts for polysulfide-iodine redox flow battery. Chinese Chemical Letters, 2026, 37(10): 111650-. doi: 10.1016/j.cclet.2025.111650

    14. [14]

      Qian Wu , Mengda Xu , Tianjiao Ma , Shuzhen Yan , Jin Li , Xuesong Jiang . Chalcone-derived oxime esters with efficient photoinitiation properties under LED irradiation. Chinese Chemical Letters, 2025, 36(3): 110427-. doi: 10.1016/j.cclet.2024.110427

    15. [15]

      Yang Li , Yanan Dong , Zhihong Wei , Changzeng Yan , Zhen Li , Lin He , Yuehui Li . Fluoride-promoted Ni-catalyzed cyanation of C–O bond using CO2 and NH3. Chinese Chemical Letters, 2025, 36(5): 110206-. doi: 10.1016/j.cclet.2024.110206

    16. [16]

      Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257

    17. [17]

      Shicheng Dong , Jun Zhu . Could π-aromaticity cross an unsaturated system to a fully saturated one?. Chinese Chemical Letters, 2024, 35(6): 109214-. doi: 10.1016/j.cclet.2023.109214

    18. [18]

      Dongyan Ju , Hui Wang , Chuang Zhao , Jiahang Li , Luoluo Li , Xiaoyan Liu , Jie Tao , Junliang Zhang , Jinbo Zhao . A facile entry toward multi-substituted chiral cyclic nitrones and N-heterocycles via Pd-catalyzed enantioselective cyclization coupling of alkenyl oxime. Chinese Chemical Letters, 2026, 37(7): 112000-. doi: 10.1016/j.cclet.2025.112000

    19. [19]

      Man Zhao , Liwu Qiang , Zonghang Liu , Wei Wen , Ze Wang , Qilin Guo , Yanxia Zhang , Aiqin Hao , Yuhong Chang , Junming Zhang , Baoliang Lv , Xiaofang Ma , He Xiao , Jianfeng Jia . Programming selective formation of epoxy bond: Carbon dots as multifunctional mediators for steering propylene electro oxidation pathways on Ag-graphene hybrids. Chinese Chemical Letters, 2026, 37(10): 112843-. doi: 10.1016/j.cclet.2026.112843

    20. [20]

      Mingpeng Li , Yule Liu , Ziheng Jin , Zhiting Zhao , Bingbing Yan , Ziwen Wang , Qingmin Wang . Recent advances in visible-light-mediated C–S(Ⅵ) bond construction. Chinese Chemical Letters, 2026, 37(11): 112724-. doi: 10.1016/j.cclet.2026.112724

Metrics
  • PDF Downloads(21)
  • Abstract views(1867)
  • HTML views(145)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return