Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives

doi:10.6023/cjoc201702026

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2399-2408.DOI: 10.6023/cjoc201702026 Previous Articles Next Articles

Articles

3,4-二芳基-5-芳氧甲基异噁唑的合成

蒋海芳^a, 张敏^a, 张丽^a, 陈雅丽^a, 朱宁^a, 宋力平^a,b, 邓红梅^c

a 上海大学理学院化学系上海 200444;
b 中国科学院有机氟化学重点实验室上海 200032;
c 上海大学微结构重点实验室上海 200444

收稿日期:2017-02-20 修回日期:2017-04-07 发布日期:2017-05-25
通讯作者: 张敏, 宋力平 E-mail:mzhang@shu.edu.cn;lpsong@shu.edu.cn
基金资助:
国家自然科学基金（No.21272153）资助项目.

Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives

Jiang Haifang^a, Zhang Min^a, Zhang Li^a, Chen Yali^a, Zhu Ning^a, Song Liping^a,b, Deng Hongmei^c

a Department of Chemistry, School of Science, Shanghai University, Shanghai 200444;
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
c Laboratory for Microstructures, Shanghai University, Shanghai 200444

Received:2017-02-20 Revised:2017-04-07 Published:2017-05-25
Contact: 10.6023/cjoc201702026 E-mail:mzhang@shu.edu.cn;lpsong@shu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272153).

1. Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives.PDF(6850KB)

Abstract

Due to isoxazole derivatives possess a wide range of herbicidal, insecticidal and pharmacological activitives, the synthetic methodologies for preparation of isoxazole derivatives have drawn much attention in recent years. Herein, 3,4-diaryl-5-aryloxymethyl isoxazole derivatives were effectively synthesized from 3-aryl-5-(bromomethyl)isoxazole via consecutive bromination, etherification, followed by Suzuki coupling reaction catalyzed by Pd(PPh₃)₂Cl₂. Preliminary bioassay data showed that some of the title compounds exhibited certain insecticidal activities against Oriental armyworm.

Key words: isoxazole derivatives, bromination, etherification, suzuki coupling reaction

Cite this article

Jiang Haifang, Zhang Min, Zhang Li, Chen Yali, Zhu Ning, Song Liping, Deng Hongmei. Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives[J]. Chin. J. Org. Chem., 2017, 37(9): 2399-2408.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Castellano, S.; Kuck, D.; Viviano, M.; Yoo, J.; Lope?-Vallejo, F.; Conti, P.; Tamborini, L.; Pinto, A.; Medina-Franco, J. L.; Sbardella, G. J. Med. Chem. 2011, 54, 7663.
[2] Kumar, K. A.; Jayaroopa, P. Chem. Biol. Sci. 2013, 3, 294.
[3] Dong, K. Y.; Qin, H. T.; Bao, X. X.; Liu, F.; Zhu, C. Org. Lett. 2014, 16, 5266.
[4] Pere?, J. M.; Ramon, D. J. ACS Sustainable Chem. Eng. 2015, 3, 2343.
[5] Fan, Y. J. Agrochem. Res. Appl. 2010, 14, 1(in Chinese) (范玉杰, 农药研究与应用, 2010, 14, 1.)
[6] He, H. W.; Li, M. Q.; Huang, G. L. Agrochemicals 2000, 39, 4(in Chinese) (贺红武, 李美强, 黄刚良, 农药, 2000, 39, 4.)
[7] Eccles, S. A.; Massey, A.; Raynaud, F. I.; Sharp, S. Y.; Box, G.; Valenti, M.; Patterson, L.; Brandon, A. D. H.; Gowan, S.; Boxall, F.; Aherne, W.; Rowlands, M.; Hayes, A.; Martins, V.; Urban, F.; Boxall, K.; Prodromou, C.; Pearl, L.; James, K.; Matthews, T. P.; Cheung, K. M.; Kalusa, A.; Jones, K.; McDonald, E.; Barril, X.; Brough, P. A.; Cansfield, J. E.; Dymock, B.; Drysdale, M. J.; Finch, H.; Howes, R.; Hubbard, R. E.; Surgenor, A.; Webb, P.; Wood, M.; Wright, L.; Workman, P. Cancer Res. 2008, 68, 2850.
[8] Sun, R.; Li, Y.; Xiong, L.; Liu, Y.; Wang, Q. J. Agric. Food Chem. 2011, 59, 4851.
[9] Sperry, J.; Wright, D. Curr. Opin. Drug Discovery Dev. 2005, 8, 723.
[10] Lee, Y.; Koyama, Y.; Yonekawa, M.; Tanaka, T. Macromolecules 2009, 42, 7709.
[11] Masafumi, U.; Yuki, I.; Aoi, S.; Yuta, I.; Maiko, K.; Hiroko, S.; Tetsuya, M.; Takeaki, N.; Okiko, M. Tetrahedron 2011, 67, 4612.
[12] Zhou, Z. W.; Yan, J. F.; Tang, X. M. Chin. J. Org. Chem. 2010, 30, 582.
[13] Changtam, C.; Hongmanee, P.; Suksamrarn, A. Eur. J. Med. Chem. 2010, 45, 4446.
[14] John, J. T.; David, L. B.; Jeffery, S. C.; Matthew, J. G.; Carol, M. K.; Jaime, L. M.; William, E. P.; Roland, S. R.; Alexander, F. S.; Zhang, Y. Y.; Ben, S. Z.; Karen, S. J. Med. Chem. 2000, 43, 777.
[15] Yermolina, M. V.; Wang, J.; Caffrey, M. J. Med. Chem. 2011, 54, 765.
[16] Jensen, A. A.; Plath, N.; Pedersen, M. H. F.; Isberg, V.; Krall., J. J. Med. Chem. 2013, 56, 1211.
[17] Vitale, P.; Tacconelli, S.; Perrone, M. G. J. Med. Chem. 2013, 56, 4277.
[18] Fournier, P. A.; Arbour, M.; Cauchon, E. Bioorg. Med. Chem. Lett. 2012, 22, 2670.
[19] Gomha, S. M.; Badrey, M. G.; Abdalla, M. M.; Arafa, R. K. Med. Chem. Commun. 2014, 5, 1685.
[20] Crocker, C. E.; Khan, S.; Cameron, M. D.; Robertson, H. A.; Robertson, G. S.; Lograsso, P. ACS Chem. Neurosci. 2011, 2, 207.
[21] Chambers, J. W.; Pachori, A.; Howard, S.; Ganno, M.; Hansen, D.; Kamenecka, T.; Song, X.; Duckett, D.; Chen, W.; Ling, Y. Y.; Cherry, L.; Cameron, M. D.; Lin, L.; Ruiz, C. H.; Lograsso, P. ACS Chem. Neurosci. 2011, 2, 198.
[22] Kumar, D. J. S.; Ho, M. M.; Leung, J. M.; Toyokuni, T. Adv. Synth. Catal. 2002, 344, 1146.
[23] Sahoo, A. K.; Oda, T.; Nakao, Y.; Hiyama, T. Adv. Synth. Catal. 2004, 346, 1715.
[24] Fu, W. C.; Zhou, Z. Y.; Kwong, F. Y. Org. Chem. Front. 2016, 3, 273.
[25] Velcicky, J.; Soicke, A.; Steiner, R.; Schmalz, H. G. J. Am. Chem. Soc. 2011, 133, 6948.
[26] Oberli, M. A.; Buchwald, S. L. Org. Lett. 2012, 14, 4606.
[27] Scott, P. J. L.; Clarke, A.; Richardson, J. Org. Lett. 2015, 17, 476.
[28] Yang, Y.; Oldenhuis, N. J.; Buchwald, S. L. Angew. Chem. Int. Ed. 2013, 52, 615.
[29] Haag, B. A.; Sämann, C.; Jana, A.; Knochel, P. Angew. Chem. Int. Ed. 2011, 50, 7290.
[30] Piller, F. M.; Metzger, A.; Schade, M..; Haag, B. A.; Garyushin, A.; Knochel, P. Chem. Eur. J. 2009, 15, 7192.
[31] Bernhardt, S.; Manolikakes, G.; Kunz, T.; Knochel, P. Angew. Chem. Int. Ed. 2011, 50, 9205.
[32] (a) Rogers, R. S.; Talley, J. J.; Brown, D. L.; Nagarajan, S.; Carter, J. S.; Weier, R. M.; Stealey, Michael A.; Collins, Paul W.; Seibert, K. WO 9625405, 1996[Chem. Abstr. 1996, 125, 247800].
(b) Rogers, R. S.; Talley, J. J.; Sikorski, J. A.; Devadas, B.; Graneto, M. J.; Carter, J. S.; Norman, B. H.; Lu, H. F; Brown, D. L.; Nagarajan, S. WO 9638442, 1996[Chem. Abstr. 1997, 126, 104081].
[33] Yang, Y. D.; Zhang, M.; Zhu, Y. W.; Zhang, L.; Xie, Q. Q.; Song, L. P.; Deng, H. M. Chin. J. Chem. 2013, 31, 950.
[34] Xu, S. S.; Zhang, M.; Zhang, L.; Jiang, H. F.; Zhu, N.; Song, L. P.; Deng, H. M. Chin. J. Org. Chem. 2015, 35, 2595(in Chinese). (徐姗姗, 张敏, 张丽, 蒋海芳, 朱宁, 宋力平, 邓红梅, 有机化学, 2015, 35, 2595.)
[35] He, C.; He, Q.; Chen, Q.; Shi, L.; Cao, H.; Cheng, J. Tetrahedron Lett. 2010, 51, 1317.
[36] Hao, Z. S.; Li, M. J.; Lin, H. X.; Gu, Z. B.; Cui, Y. M. Dyes Pigm. 2014, 109, 54.
[37] Budzik, B. W.; Evans, K. A.; Wisnoski, D. D.; Jin, J.; Rivero, R. A.; Szewczyk, G. R.; Jayawickreme, C.; Moncol, D. L.; Yu, H. S. Bioorg. Med. Chem. Lett. 2010, 20, 1363.
[38] CCDC 1540659 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data CEntre via www.ccdc.cam.ac.uk/data_request/cif.

3,4-二芳基-5-芳氧甲基异噁唑的合成

Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Lingna Wang, Xiaoqing Liu, Gang Lin, Hongying Jin, Minjun Jiao, Xuefen Liu, Shuping Luo. Photocatalytic Activation of C(sp³)—H Bonds to Form C—S Bonds Catalyzed by (Oxybis(4,1-phenylene))bis(phenylmethanone) [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2848-2854.
[2]	Jing Wang, Linlin Wu, Qian Wang. Synthesis and Characterization of New Indeno[1,2-b]fluorene-6,12-dione Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 223-228.
[3]	Siyu Mu, Hongxia Li, Zhilin Wu, Junmei Peng, Jinyang Chen, Weimin He. Electrocatalytic Three-Component Synthesis of 4-Bromopyrazoles from Acetylacetone, Hydrazine and Diethyl Bromomalonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4292-4299.
[4]	Mengxia Zheng, Jing Zeng, Mailikezhati Meihemuti, Abudu Rexit Abulikemu. Study on the Debromination of α-Bromomethyl Ketones Catalyzed by HBr [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2121-2126.
[5]	Xia Wang, Yixin Qu, Chengyu Long, Xue-Qiang Wang. Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 795-805.
[6]	Bowen Wang, Yongjun Zhou, Shihe Luo, Xiaoyan Luo, Weiqing Chen, Shimin Yang, Zhaoyang Wang. Research Progress in C—S Bond Formation Reaction of Olefins with Organic Sulfur Reagents under Photocatalyst-Free and Non-Electrochemical Conditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 171-184.
[7]	Li Yang, Dong Shiyu, Qin Hongwei, Tang Bingyue, Gao Wentao, Chen Yu. A Facile Synthesis and M. tuberculosis Leucyl-tRNA Synthetase Inhi-bitory Activity of Novel 3-Arylvinylquinoxaline-2-carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2817-2826.
[8]	Wang Ligeng, Yu Qin, Feng Chun, Zhang Yan, Hu Jun. Efficient Synthesis of Dibromoalkanes and Iodoacetates from Olefins Using ZnAl-XO₃^--LDHs/LiX (X=Br, I) as Halogen Sources [J]. Chin. J. Org. Chem., 2019, 39(6): 1787-1793.
[9]	Zhu Fuyuan, Wang Yanmei, He Mingchuang, Yan Zhaohua, Lin Sen. Tetrabutylammonium Iodide Promoted Thioetherification of Arylsulfonylhydrazides with 4-Hydroxycoumarins [J]. Chin. J. Org. Chem., 2019, 39(4): 1175-1180.
[10]	Fan Weiyong, Yu Lei, Peng Xiangjun, Liu Liangxian. In the Presence of FeCl₃ Reaction of Alknols with Iodine: A Convenient Synthetic Route to Iodocyclic Ethers [J]. Chin. J. Org. Chem., 2017, 37(4): 920-924.
[11]	Feng Cuilan, Hei Liying, Li Zhen, Liu Lantao. Magnetic Microporous Organic Polymer of 1,1'-Bi-2-naphtholSupported Palladium for Suzuki Coupling Reactions [J]. Chin. J. Org. Chem., 2016, 36(1): 179-184.
[12]	Hei Liying, Feng Cuilan, Li Zhen, Liu Lantao, Gui Jianzhou. Microporous Network Polyaniline Coated Magnetic Fe₃O₄ Nanoparticals Supported Palladium Catalyzed Suzuki and Heck Coupling Reactions [J]. Chin. J. Org. Chem., 2015, 35(8): 1673-1681.
[13]	Sun Jing, Peng Xinhua, Guo Hao. Studies on Photoinduced Carbon-Silicon Bond Cleavage and Subsequent Bromination Reaction [J]. Chin. J. Org. Chem., 2015, 35(6): 1375-1379.
[14]	Guan Litao, Mo Guangzhen, Wu Yancheng, Liang Xinyu, Luo Qiaofang, Wang Zhaoyang. Synthesis of 2(5H)-Furanone Derivatives with Biphenyl Ether Unit [J]. Chin. J. Org. Chem., 2015, 35(5): 1081-1089.
[15]	Li Peiyuan, Zhang Jianrui, Guo Shenghai, Zhang Xinying, Fan Xuesen. New Synthesis of Brivudine and Its Analogs [J]. Chin. J. Org. Chem., 2015, 35(4): 910-916.