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

a.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

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.
- isoxazole,
- iodine,
- α, β-unsaturated oxime,
- C-O bond formation
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
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]
  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
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]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274
15. [15]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
16. [16]
  Jinli Chen , Shouquan Feng , Tianqi Yu , Yongjin Zou , Huan Wen , Shibin Yin . Modulating Metal-Support Interaction Between Pt3Ni and Unsaturated WOx to Selectively Regulate the ORR Performance. Chinese Journal of Structural Chemistry, 2023, 42(10): 100168-100168. doi: 10.1016/j.cjsc.2023.100168
17. [17]
  Longlong Geng , Huiling Liu , Wenfeng Zhou , Yong-Zheng Zhang , Hongliang Huang , Da-Shuai Zhang , Hui Hu , Chao Lv , Xiuling Zhang , Suijun Liu . Construction of metal-organic frameworks with unsaturated Cu sites for efficient and fast reduction of nitroaromatics: A combined experimental and theoretical study. Chinese Chemical Letters, 2024, 35(8): 109120-. doi: 10.1016/j.cclet.2023.109120
18. [18]
  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
19. [19]
  Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
20. [20]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(746)
HTML views(31)

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

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

Metrics

通讯作者: 陈斌, bchen63@163.com

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