Catalytic Nucleophilic Addition of 3, 5-Dialkyl-4-nitroisoxazoles to Trifluoromethyl Ketones on Water

doi:10.6023/cjoc201709049

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1155-1164.DOI: 10.6023/cjoc201709049 Previous Articles Next Articles

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水相催化3,5-二烷基-4-硝基异噁唑与三氟甲基酮的亲核加成反应

王晶晶, 李峰, 徐妍, 王娟, 武紫燕, 杨成玉, 刘澜涛

商丘师范学院化学化工学院药物绿色合成河南省工程实验室商丘 476000

收稿日期:2017-09-29 修回日期:2017-12-29 发布日期:2018-01-26
通讯作者: 王晶晶,E-mail:wangjingjing0918@163.com;刘澜涛,E-mail:liult05@iccas.ac.cn E-mail:wangjingjing0918@163.com;liult05@iccas.ac.cn
基金资助:
国家自然科学基金（Nos.21402116，21502111，21572126）、河南省重点科技攻关项目（No.172102210099）和河南省高等学校重点科研（No.15A150072）资助项目.

Catalytic Nucleophilic Addition of 3, 5-Dialkyl-4-nitroisoxazoles to Trifluoromethyl Ketones on Water

Wang Jingjing, Li Feng, Xu Yan, Wang Juan, Wu Ziyan, Yang Chengyu, Liu Lantao

Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000

Received:2017-09-29 Revised:2017-12-29 Published:2018-01-26
Contact: 10.6023/cjoc201709049 E-mail:wangjingjing0918@163.com;liult05@iccas.ac.cn
Supported by:
Project supported by the National Natural Sciences Foundation of China (Nos. 21402116, 21502111, 21572126), the Key Scientific and Technological Project of Henan Province (No. 172102210099) and the Key Science Research of Education Committee in Henan Province (No. 15A150072).

1. Catalytic Nucleophilic Addition of 3, 5-Dialkyl-4-nitroisoxazoles to Trifluoromethyl Ketones on Water.PDF(1042KB)

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Wang Jingjing, Li Feng, Xu Yan, Wang Juan, Wu Ziyan, Yang Chengyu, Liu Lantao. Catalytic Nucleophilic Addition of 3, 5-Dialkyl-4-nitroisoxazoles to Trifluoromethyl Ketones on Water[J]. Chin. J. Org. Chem., 2018, 38(5): 1155-1164.

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[1] (a) Welch, J. T.; Eswarakrishman, S. Fluorine in Bioorganic Chemistry, Wiley, New York, 1991.
(b) Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993.
(c) Banks, R. E.; Smart, B. E.; Tatlow, C. J. Organofluorine Chemistry:Principles and Comercial Applications, Springer, New York, 1994.
(d) Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu, M. Organofluorine Compounds:Chemistry and Applications, Springer-Verlag, Berlin, 2000.
(e) Kirsch, P. Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2005.
(f) Uneyama, K. Organofluorine Chemistry, Blackwell, Oxford, 2007.
(g) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, 2009.
[2] (a) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013.
(b) Mîller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(c) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(d) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
(e) Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496.
(f) Ojima, I. J. Org. Chem. 2013, 78, 6358.
(g) Fujiwara, T.; O_Hagan, D. J. Fluorine Chem. 2014, 167, 16.
(h) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(i) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
[3] (a) Pierce, M. E.; Rodney, L. P. J.; Radesca, L. A.; Lo, Y. S.; Silverman, S.; Moore, J. R.; Islam, Q.; Choudhury, A.; Fortunak, J. M. D.; Nguyen, D.; Luo, C.; Morgan, S. J.; Davis, W. P.; Confalone, P. N.; Chen, C.-Y.; Tillyer, R. D.; Frey, L.; Tan, L.; Xu, F.; Zhao, D.; Thompson, A. S.; Corley, E. G.; Grabowski, E. J. J.; Reamer, R.; Reider, P. J. J. Org. Chem. 1998, 63, 8536.
(b) Corbett, J. W.; Ko, S. S.; Rodgers, J. D.; Gearhart, L. A.; Magnus, N. A.; Bacheler, L. T.; Diamond, S.; Jeffrey, S.; Klabe, R. M.; Cordova, B. C.; Garber, S.; Logue, K.; Trainor, G. L.; Anderson, P. S.; Erickson-Viitanen, S. K. J. Med. Chem. 2000, 43, 2019.
[4] Schenck, H. A.; Lenkowski, P. W.; Choudhury-Mukherjee, I.; Ko, S.-H.; Stables, J. P.; Patel, M. K.; Brown, M. L. Bioorg. Med. Chem. 2004, 12, 979.
[5] Fandrick, D. R.; Reeves, J. T.; Bakonyi, J. M.; Nyalapatla, P. R.; Tan, Z.; Niemeier, O.; Akalay, D.; Fandrick, K. R.; Wohlleben, W.; Ollenberger, S.; Song, J. J.; Sun, X.; Qu, B.; Haddad, N.; Sanyal, S.; Shen, S.; Ma, S.; Byrne, D.; Chitroda, A.; Fuchs, V.; Narayanan, B. A.; Grinberg, N.; Lee, H.; Yee, N.; Brenner, M.; Senanayake, C. H. J. Org. Chem. 2013, 78, 3592.
[6] (a) Betageri, R.; Zhang, Y.; Zindell, R. M.; Kuzmich, D.; Kirrane, T. M.; Bentzien, J.; Cardozo, M.; Capolino, A. J.; Fadra, T. N.; Nelson, R. M.; Paw, Z.; Shih, D.-T.; Shih, C.-K.; Zuvela-Jelaska, L.; Nebozny, G.; Thomson, D. Bioorg. Med. Chem. Lett. 2005, 15, 4761.
(b) Barker, M.; Clackers, M.; Copley, R.; Demaine, D. A.; Humphreys, D.; Inglis, G. G. A.; Johnston, M. J.; Jones, H. T.; Haase, M. V.; House, D.; Loiseau, R.; Nisbet, L.; Pacquet, F.; Skone, P. A.; Shanahan, S. E.; Tape, D.; Vinader, V. M.; Washington, M.; Uings, I.; Upton, R.; McLay, I. M.; Macdonald, S. J. F. J. Med. Chem. 2006, 49, 4216.
[7] (a) Sani, M.; Viani, F.; Binda, M.; Zaffaroni, N.; Zanda, M. Lett. Org. Chem. 2005, 2, 447.
(b) Betageri, R.; Gilmore, T.; Kuzmich, D.; Kirrane, T. M.; Bentzien, J.; Wiedenmayer, D.; Bekkali, Y.; Regan, J.; Berry, A.; Latli, B.; Kukulka, A. J.; Fedra, T. N.; Nelson, R. N.; Goldrick, S.; Zuvela-Jelaska, L.; Souza, D.; Pelletier, J.; Dinallo, R.; Panzenbeck, M.; Torcellini, C.; Lee, H.; Pack, E.; Harcken, C.; Nabozny, G.; Thomson, D. S. Bioorg. Med. Chem. Lett. 2011, 21, 6842.
[8] Carceller, E.; Merlos, M.; Giral, M.; Balsa, D.; Garciía-Rafanell, J.; Forn, J. J. Med. Chem. 1996, 39, 487.
[9] For reviews, see:(a) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
(b) Kelly, C. B.; Mercadante, M. A.; Leadbeater, N. E. Chem. Commun. 2013, 49, 11133.
[10] For selected examples:(a) Hara, N.; Tamura, R.; Funahashi, Y.; Nakamura, S. Org. Lett. 2011, 13, 1662.
(b) Zhang, G.-W.; Meng, W.; Ma, H.; Nie, J.; Zhang, W.-Q.; Ma, J.-A. Angew. Chem., Int. Ed. 2011, 50, 3538.
(c) Cui, H.-F.; Wang, L.; Yang, L.-J.; Nie, J.; Zheng, Y.; Ma, J.-A. Tetrahedron 2011, 67, 8470.
(d) Li, X.-J.; Xiong, H.-Y.; Hua, M.-Q.; Nie, J.; Zheng, Y.; Ma, J.-A. Tetrahedron Lett. 2012, 53, 2117.
(e) Zheng, Y.; Xiong, H.-Y.; Nie, J.; Hua, M.-Q.; Ma, J.-A. Chem. Commun. 2012, 48, 4308.
(f) Luo, R.; Li, K.; Hu, Y.; Tang, W. Adv. Synth. Catal. 2013, 355, 1297.
(g) Zong, H.; Huang, H.; Bian, G.; Song, L. J. Org. Chem. 2014, 79, 11768.
(h) Wang, L.; Liu, N.; Dai, B.; Ma, X.; Shi, L. RSC Adv. 2015, 5, 10089.
(i) Jamal, Z.; Teo, Y.-C. RSC Adv. 2015, 5, 26949.
(j) Zhang, D.; Tanaka, F. Adv. Synth. Catal. 2015, 357, 3458.
(k) Tao, R.; Yin, X.-J.; Wang, K.-H.; Niu, Y.-Z.; Wang, Y.-L.; Huang, D.-F.; Su, Y.-P.; Wang, J.-X.; Hu, Y.-L.; Fu, Y.; Du, Z.-Y. Chin. Chem. Lett. 2015, 26, 1046.
(l) Jing, Z.; Bai, X.; Chen, W.; Zhang, G.; Zhu, B.; Jiang, Z. Org. Lett. 2016, 18, 260.
(m) Lutete, L. M.; Miyamoto, T.; Ikemoto, T. Tetrahedron Lett. 2016, 57, 1220.
(n) Cook, A. M.; Wolf, C. Angew. Chem., Int. Ed. 2016, 55, 2929.
(o) Lee, K.; Silverio, D. L.; Torker, S.; Robbins, D. W.; Haeffner, F.; Mei, F. W.; Hoveyda, A. H. Nat. Chem. 2016, 8, 768.
(p) Matador, E.; Monge, D.; Fernández, R.; Lassaletta, J. M. Green Chem. 2016, 18, 4042.
(q) Mszar, N. W.; Mikus, M. S.; Torker, S.; Haeffner, F.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2017, 56, 8736.
(r) Noda, H.; Amemiya, F.; Weidner, K.; Kumagai, N.; Shibasaki, M. Chem. Sci. 2017, 8, 3260.
(s) Bai, X.; Zeng, G.; Shao, T.; Jiang, Z. Angew. Chem., Int. Ed. 2017, 56, 3684.
(t) Zheng, Y.; Tan, Y.; Harms, K.; Marsch, M.; Riedel, R.; Zhang, L.; Meggers, E. J. Am. Chem. Soc. 2017, 139, 4322.
[11] Bandini, M.; Sinisi, R. Org. Lett. 2009, 11, 2093.
[12] Zhang, Y.; Wei, B.-W.; Zou, L.-N.; Kang, M.-L.; Luo, H.-Q.; Fan, X.-L. Tetrahedron 2016, 72, 2472.
[13] Czerwinski, P.; Molga, E.; Cavallo, L.; Poater, A.; Michalak, M. Chem. Eur. J. 2016, 22, 8089.
[14] (a) Grieco, P. A. Organic Synthesis in Water, Blackie, London, 1998.
(b) Lindstrom, U. M. Organic Reactions in Water:Principles, Strategies and Applications, Blackwell, Oxford, U. K., 2007.
(c) Li, C.-J.; Chan, T.-H. Comprehensive Organic Reactions in Aqueous Media, Wiley, New York, 2007.
[15] For selected reviews:(a) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
(b) Head-Gordon, T.; Hura, G. Chem. Rev. 2002, 102, 2651.
(c) Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 8103.
(d) Mase, N.; Barbas Ⅲ, C. F. Org. Biomol. Chem. 2010, 8, 4043.
[16] For selected reviews:(a) Li, C.-J. Chem. Rev. 2005, 105, 3095.
(b) Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68.
(c) Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.
(d) Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302.
(e) Simon, M.-O.; Li, C.-J. Chem. Soc. Rev. 2012, 41, 1415.
(f) Gawande, M. B.; Bonifacio, V. D. B.; Luque, R.; Branco, P. S.; Varma, R. S. Chem. Soc. Rev. 2013, 42, 5522.
(g) Levin, E.; Ivry, E.; Diesendruck, C. E.; Lemcoff, N. G. Chem. Rev. 2015, 115, 4607.
(h) Butler, R. N.; Coyne, A. G. Org. Biomol. Chem. 2016, 14, 9945.
[17] For selected examples:(a) Phippen, C. B. W.; Beattie, J. K.; McErlean, C. S. P. Chem. Commun. 2010, 46, 8234.
(b) Fu, X.-P.; Liu, L.; Wang, D.; Chen, Y.-J.; Li, C.-J. Green. Chem. 2011, 13, 549.
(c) Sakakura, A.; Koshikari, Y.; Akakura, M.; Ishihara, K. Org. Lett. 2011, 14, 30.
(d) Paladhi, S.; Chauhan, A.; Dhara, K.; Tiwari, A. K.; Dash, J. Green. Chem. 2012, 14, 2990.
(e) Islam, S.; Larrosa, I. Chem. Eur. J. 2013, 19, 15093.
(f) Sengoden, M.; Punniyamurthy, T. Angew. Chem. Int. Ed. 2013, 52, 572.
(g) Paladhi, S.; Bhati, M.; Panda, D.; Dash, J. J. Org. Chem. 2014, 79, 1473.
(h) Thakur, P. B.; Meshram, H. M. RSC Adv. 2014, 4, 5343.
(i) Thakur, P. B.; Meshram, H. M. RSC Adv. 2014, 4, 6019.
(j) Yu, J.-S.; Liu, Y.-L.; Tang, J.; Wang, X.; Zhou, J. Angew. Chem. Int. Ed. 2014, 53, 9512.
(k) Yang, F.; Klumphu, P.; Liang, Y.-M.; Lipshutz, B. H. Chem. Commun. 2014, 50, 936.
(l) Zhang, F.-Z.; Tian, Y.; Li, G.-X.; Qu, J. J. Org. Chem. 2015, 80, 1107.
(m) SaiPrathima, P.; Srinivas, K.; Mohan Rao, M. Green. Chem. 2015, 17, 2339.
(n) Bhattacharjya, A.; Klumphu, P.; Lipshutz, B. H. Nat. Commun. 2015, 6, 7401.
(o) Cho, B. S.; Chung, Y. K. Chem. Commun. 2015, 51, 14543.
(p) Xiao, J.; Wen, H.; Wang, L.; Xu, L.; Hao, Z.; Shao, C.-L.; Wang, C.-Y. Green Chem. 2016, 18, 1032.
(q) Zhang, Y.; Wei, B.-W.; Lin, H.; Zhang, L.; Liu, J.-X.; Luo, H.-Q.; Fan, X.-L. Green Chem. 2015, 17, 3266.
(r) Ren, N.; Nie, J.; Ma, J.-A. Green Chem. 2016, 18, 6609.
[18] (a) Wang, J.; Kong, W.-G.; Li, F.; Liu, J.; Shen, Q.; Liu, L.; Zhao, W.-X. Org. Biomol. Chem. 2015, 13, 5399.
(b) Li, F.; Wang, J.; Xu, M.; Zhao, X.; Zhou, X.; Zhao, W.-X.; Liu, L. Org. Biomol. Chem. 2016, 14, 3981.
(c) Wang, J.; Li, F.; Shen, Q.; Pei, W.; Zhao, W.-X.; Liu, L. Synthesis 2016, 48, 441.
(d) Wang, J.; Li, F.; Xie, H.; Xu, M.; Zhao, X.; Liu, L.; Zhao, W.-X. Appl. Organomet. Chem. 2017, 31, e3545.
[19] CCDC 1558716(3a) and CCDC 1559048(5) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
[20] (a) Creary, X. J. Org. Chem. 1987, 52, 5026.
(b) Chong, J. M.; Mar, E. K. J. Org. Chem. 1991, 56, 893.
(c) Prakash, G. K. S.; Panja, C.; Vaghoo, H.; Surampudi, V.; Kultyshev, R.; Mandal, M.; Rasul, G.; Mathew, T.; Olah, G. A. J. Org. Chem. 2006, 71, 6806.
(d) Cheng, H.; Pei, Y.; Leng, F.; Li, J.; Liang, A.; Zou, D.; Wu, Y.; Wu, Y. Tetrahedron Lett. 2013, 54, 4483.
[21] (a) Adamo, M. F. A.; Duffy, E. F. Org. Lett. 2006, 8, 5157.
(b) Adamo, M. F. A.; Suresh, S. Tetrahedron 2009, 65, 990.
(c) Zhang, J.; Liu, X.; Ma, X.; Wang, R. Chem. Commun. 2013, 49, 9329.
[22] Gao, J.-R.; Wu, H.; Xiang, B.; Yu, W.-B.; Han, L.; Jia, Y.-X. J. Am. Chem. Soc. 2013, 135, 2983.
[23] Fiandra, C. D.; Piras, L.; Fini, F.; Disetti, P.; Moccia, M.; Adamo, M. F. A. Chem. Commun. 2012, 48, 3863.
[24] McBee, E. T.; Kim, Y. S.; Braendlin, H. P. J. Am. Chem. Soc. 1962, 84, 3154.

水相催化3,5-二烷基-4-硝基异噁唑与三氟甲基酮的亲核加成反应

Catalytic Nucleophilic Addition of 3, 5-Dialkyl-4-nitroisoxazoles to Trifluoromethyl Ketones on Water

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