“水上”吡唑啉酮与三氟甲基酮的亲核加成

doi:10.6023/cjoc201910038

摘要/Abstract

基于水相条件下发展了一种绿色高效的吡唑啉酮与三氟甲基酮的亲核加成的方法，且以高收率获得吡唑啉酮取代的叔三氟甲基醇类化合物.该方法具有的无催化剂、无色谱柱分离、环境友好以及易于后处理的优点使其在制备各种吡唑啉酮取代的叔三氟甲基醇类化合物中很有应用前景.

关键词: “水上”反应, 亲核加成, 吡唑啉酮, 三氟甲基酮

A green and efficient nucleophilic addition reaction of trifluoromethyl ketone with pyrazolone was developed under "on water" conditions, affording pyrazolone substituted tertiary trifluoromethyl alcohols in high yields. The advantages of being catalyst-free, column chromatography-free, environmentally benign and easy workup make it a promising method for preparation of a variety of pyrazolone substituted tertiary trifluoromethyl alcohols.

Key words: “on water” reaction, nucleophilic addition, pyrazolone, trifluoromethyl ketone

引用此文

罗亮, 曹晓梅, 赖国伟, 刘金香, 罗海清, 路东亮, 张勇. “水上”吡唑啉酮与三氟甲基酮的亲核加成[J]. 有机化学, 2020, 40(5): 1323-1330.

Luo Liang, Cao Xiaomei, Lai Guowei, Liu Jinxiang, Luo Haiqing, Lu Dongliang, Zhang Yong. “On Water” Nucleophilic Addition of Pyrazolones to Trifluoromethyl Ketones[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1323-1330.

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参考文献

[1] (a) Trost, B. M. Angew. Chem. Int. Ed. 1995, 34, 259.
(b) Anastas, P. T.; Williamson, T. C. Green Chemistry:Frontiers in Chemical Synthesis and Processes, Oxford University Press, Oxford, 1998.
(c) Li, C. J. Chem. Rev. 2005, 105, 3095.
(d) Sheldon, R. A. Green Chem. 2005, 7, 267.
(e) Gawande, M. B.; Bonifacio, V. D.; Luque, R.; Branco, P. S.; Varma, R. S. Chem. Soc. Rev. 2013, 42, 5522.
[2] (a) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
(b) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
(c) Horvath, I. T.; Anastas, P. T. Chem. Rev. 2007, 107, 2167.
(d) Niu, R.; Xiao, J.; Liang, T.; Li, X. Org. Lett. 2012, 14, 676.
(e) Shen, Z. L.; Wang, S. Y.; Chok, Y. K.; Xu, Y. H.; Loh, T. P. Chem. Rev. 2013, 113, 271.
(f) Butler, R. N.; Coyne, A. G. Org. Biomol. Chem. 2016, 14, 9945.
(g) Xiao, J.; Wen, H.; Wang, L.; Xu, L.; Hao, Z.; Shao, C.-L.; Wang, C.-Y. Green Chem. 2016, 18, 1032.
(h) Guo, W.; Liu, X.; Liu, Y.; Li, C. ACS Catal. 2017, 8, 328.
(i) Kitanosono, T.; Masuda, K.; Xu, P.; Kobayashi, S. Chem. Rev. 2018, 118, 679.
(j) Xie, P.; Wang, J.; Liu, Y.; Fan, J.; Wo, X.; Fu, W.; Sun, Z.; Loh, T. P. Nat. Commun. 2018, 9, 1321.
(k) Han, J.; Zhang, J.-L.; Zhang, W.-Q.; Gao, Z.; Xu, L.-W.; Jian, Y. J. Org. Chem. 2019, 84, 7642.
(l) Wang, W.; Wang, S. X.; Qin, X. Y.; Li, J. T. Synth. Commun. 2005, 35, 1263.
(m) Wang, A.-Q.; Jin, T.-S.; Cheng, Z.-L.; Li, T.-S. Asian J. Chem. 2010, 22, 1973.
(n) Thakur, P. B.; Meshram, H. M. RSC Adv. 2014, 4, 6019.
(o) Zhou, Z.; Duan, J. F.; Mu, X. J.; Xiao, X. Y. Chin. J. Org. Chem. 2018, 38, 585(in Chinese). (周曌, 段建凤, 穆小静, 肖尚友, 有机化学, 2018, 38, 585.)
(p) Hu, X. Y.; Yu, H. F.; Wang, W. J.; Jiang, S. Q.; Liu, Q.; He, J. Chin. J. Org. Chem. 2019, 39, 3183(in Chinese). (胡小宇, 于海丰, 王文举, 姜思傲, 刘奇, 何洁, 有机化学, 2019, 39, 3183.)
[3] (a) Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275.
(b) Paladhi, S.; Chauhan, A.; Dhara, K.; Tiwari, A. K.; Dash, J. Green Chem. 2012, 14, 2990.
(c) Paladhi, S.; Bhati, M.; Panda, D.; Dash, J. J. Org. Chem. 2014, 79, 1473.
(d) Yu, J. S.; Liu, Y. L.; Tang, J.; Wang, X.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53, 9512.
(e) Zhang, Y.; Wei, B. W.; Lin, H.; Zhang, L.; Liu, J. X.; Luo, H. Q.; Fan, X. L. Green Chem. 2015, 17, 3266.
(f) SaiPrathima, P.; Srinivas, K.; Rao, M. M. Green Chem. 2015, 17, 2339.
(g) Luque-Agudo, V.; Gil, M. V.; Roman, E.; Serrano, J. A. Green Chem. 2016, 18, 3844.
(h) Balaraman, K.; Ding, R.; Wolf, C. Adv. Synth. Catal. 2017, 359, 4165.
(i) Dilauro, G.; Dell'Aera, M.; Vitale, P.; Capriati, V.; Perna, F. M. Angew. Chem., Int. Ed. 2017, 56, 10200.
(j) Zhu, S.; Chen, C. Q.; Xiao, M. Y.; Yu, L. P.; Wang, L.; Xiao, J. Green Chem. 2017, 19, 5653.
(k) Hajra, S.; Singha Roy, S.; Aziz, S. M.; Das, D. Org. Lett. 2017, 19, 4082.
(l) Hikawa, H.; Ichinose, R.; Kikkawa, S.; Azumaya, I. Green Chem. 2018, 20, 1297.
(m) Hikawa, H.; Ichinose, R.; Kikkawa, S.; Azumaya, I. A. J. Org. Chem. 2018, 7, 416.
(n) Wang, Z.; Cui, Y.-T.; Xu, Z.-B.; Qu, J. J. Org. Chem. 2008, 73, 2270.
[4] (a) Rideout, D. C.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 7816.
(b) Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275.
[5] (a) Gouverneur, V.; Müller, K. In Fluorine in Pharmaceutical and Medicinal Chemistry:From Biophysical Aspects to Clinical Applications, Imperial College Press, London, 2012.
(b) Jeschke, P. Pest Manage. Sci. 2010, 66, 10.
(c) Lectard, S.; Hamashima, Y.; Sodeoka, M. Adv. Synth. Catal. 2010, 352, 2708.
(d) Ni, C.; Hu, J. Chem. Soc. Rev. 2016, 45, 5441.
(e) Politanskaya, L. V.; Selivanova, G. A.; Panteleeva, E. V.; Tretyakov, E. V.; Platonov, V. E.; Nikul'shin, P. V.; Vinogradov, A. S.; Zonov, Y. V.; Karpov, V. M.; Mezhenkova, T. V.; Vasilyev, A. V.; Koldobskii, A. B.; Shilova, O. S.; Morozova, S. M.; Burgart, Y. V.; Shchegolkov, E. V.; Saloutin, V. I.; Sokolov, V. B.; Aksinenko, A. Y.; Nenajdenko, V. G.; Moskalik, M. Y.; Astakhova, V. V.; Shainyan, B. A.; Tabolin, A. A.; Ioffe, S. L.; Muzalevskiy, V. M.; Balenkova, E. S.; Shastin, A. V.; Tyutyunov, A. A.; Boiko, V. E.; Igumnov, S. M.; Dilman, A. D.; Adonin, N. Y.; Bardin, V. V.; Masoud, S. M.; Vorobyeva, D. V.; Osipov, S. N.; Nosova, E. V.; Lipunova, G. N.; Charushin, V. N.; Prima, D. O.; Makarov, A. G.; Zibarev, A. V.; Trofimov, B. A.; Sobenina, L. N.; Belyaeva, K. V.; Sosnovskikh, V. Y.; Obydennov, D. L.; Usachev, S. A. Russ. Chem. Rev. 2019, 88, 425.
(f) Ren, Z. W.; Ren, N.; Zhang, F. G.; Ma, J. A. Acta Chim. Sin. 2018, 76, 940(in Chinese). (任智雯, 任楠, 张发光, 马军安, 化学学报, 2018, 76, 940.)
(g) Hu, J. J.; Huang, Y. G.; Xu, X. H.; Qin, F. L. Chin. J. Org. Chem. 2019, 39, 177(in Chinese). (胡娟娟, 黄焰根, 徐修华, 卿凤翎, 有机化学, 2019, 39, 177.)
[6] (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(c) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
[7] (a) Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 4959.
(b) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
(c) Feng, Z.; Min, Q.-Q.; Xiao. Y.-L.; Zhang, B.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 1669.
(d) Zhou, D.; Huang, Z.; Yu, X.; Wang, Y.; Li, J.; Wang, W.; Xie, H. Org. Lett. 2015, 17, 5554.
(e) Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731.
(f) Wang, L.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2015, 54, 15414.
(g) Huang, Y.-Y.; Yang, X.; Chen, Z.; Verpoort, F.; Shibata, N. Chem.-Eur. J. 2015, 21, 8664.
(h) Montesinos-Magraner, M.; Vila, C.; Blay, G.; Fernández, I.; Muñoz, M. C.; Pedro, J. R. Adv. Synth. Catal. 2015, 357, 3047.
(i) Feng, Z.; Min, Q.-Q.; Zhao, H.-Y.; Gu, J.-W.; Zhang, X. Angew. Chem., Int. Ed. 2015, 54, 1270.
(j) Lou, H. Q.; Wang, Y.; Jin, E.; Lin, X. J. Org. Chem. 2016, 81, 2019.
(k) Cook, A. M.; Wolf, C. Angew. Chem., Int. Ed. 2016, 55, 2929.
(l) Zhang, Z. M.; Xu, B.; Xu, S.; Wu, H. H.; Zhang, J. Angew. Chem., Int. Ed. 2016, 55, 6324.
(m) Feng, Z.; Min, Q.-Q.; Zhang, X. Org. Lett. 2016, 18, 44.
(n) Duan, J.; Cheng, Y.; Cheng, J.; Li, R.; Li, P. Chem.-Eur. J. 2017, 23, 519.
(o) Holmes, M.; Nguyen, K. D.; Schwartz, L. A.; Luong, T.; Krische, M. J. J. Am. Chem. Soc. 2017, 139, 8114.
(p) Xie, E.; Rahman, A.; Lin, X. Org. Chem. Front. 2017, 4, 1407.
(q) Xu, B.; Zhang, Z.-M.; Xu, S.; Liu, B.; Xiao, Y.; Zhang, J. ACS Catal. 2017, 7, 210.
(r) Feng, Z.; Min, Q.-Q.; Fu, X.-P.; An, L.; Zhang, X. Nat. Chem. 2017, 9, 918.
(s) Feng, Z.; Xiao, Y.-L.; Zhang, X. Acc. Chem. Res. 2018, 51, 2264.
(t) Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815(in Chinese). (卿凤翎, 有机化学, 2012, 32, 815.)
(u) Zhang, F. G.; Peng, X.; Ma, J. A. Chin. J. Org. Chem. 2019, 39, 109(in Chinese). (张发光, 彭星, 马军安, 有机化学, 2019, 39, 109.)
[8] (a) Gursoy, A.; Demirayak, S.; Capan, G.; Erol, K.; Vural, K. Eur. J. Med. Chem. 2000, 35, 359.
(b) Rubtsov, A. E.; Makhmudov, R. R.; Kovylyaeva, N. V.; Prosyanik, N. I.; Bobrov, A. V.; Zalesov, V. V. Pharm. Chem. J. 2002, 36, 608.
(c) Nishio, M.; Matsuda, M.; Ohyanagi, F.; Sato, Y.; Okumura, S.; Tabata, D.; Morikawa, A.; Nakagawa, K.; Horai, T. Lung Cancer 2005, 49, 245.
(d) Bondock, S.; Rabie, R.; Etman, H. A.; Fadda, A. A. Eur. J. Med. Chem. 2008, 43, 2122.
(e) Rostom, S. A.; el-Ashmawy, I. M.; Abd el Razik, H. A.; Badr, M. H.; Ashour, H. M. Bioorg. Med. Chem. 2009, 17, 882.
(f) Bayrak, H.; Demirbas, A.; Demirbas, N.; Karaoglu, S. A. Eur. J. Med. Chem. 2010, 45, 4726.
(g) Fustero, S.; Sanchez-Rosello, M.; Barrio, P.; Simon-Fuentes, A. Chem Rev. 2011, 111, 6984.
(h) Li, J.-H.; Du, D.-M. Org. Biomol. Chem. 2013, 11, 6215.
(i) Ansari, A.; Ali, A.; Asif, M.; Shamsuzzaman. New J. Chem. 2017, 41, 16.
(j) Liu, S.; Bao, X.; Wang, B. Chem. Commun. 2018, 54, 11515.
[9] (a) Jung, Y. S.; Marcus, R. A. J. Am. Chem. Soc. 2007, 129, 5492.
(b) Thomas, L. L.; Tirado-Rives, J.; Jorgensen, W. L. J. Am. Chem. Soc. 2010, 132, 3097.
(c) Manna, A.; Kumar, A. J. Phys. Chem. A 2013, 117, 2446.
(d) Sela, T.; Vigalok, A. Org. Lett. 2014, 16, 1964.
[10] (a) Kelly, C. B.; Mercadante, M. A.; Hamlin, T. A.; Fletcher, M. H.; Leadbeater, N. E. J. Org. Chem. 2012, 77, 8131.
(b) Martinelli, E.; Vicini, A. C.; Mancinelli, M.; Mazzanti, A.; Zani, P.; Bernardi, L.; Fochi, M. Chem. Commun. 2015, 51, 658.
[11] (a) Rassu, G.; Zambrano, V.; Pinna, L.; Curti, C.; Battistini, L.; Sartori, A.; Pelosi, G.; Casiraghi, G.; Zanardi, F. Adv. Synth. Catal. 2014, 356, 2330.
(b) Zhu, Y.-F.; Wei, B.-L.; Wei, J.-J.; Wang, W.-Q.; Song, W.-B.; Xuan, L.-J. Tetrahedron Lett. 2019, 60, 1202.
(c) Stefane B.; Polanc S. Tetrahedron 2007, 63, 10902.
(d) MacLean, M. A.; Diez-Cecilia, E.; Lavery, C. B.; Reed, M. A.; Wang, Y. F.; Weaver, D. F.; Stradiotto, M. Bioorg. Med. Chem. Lett. 2016, 26, 100.
(e) Nishi, H.; Watanabe, T.; Yuki, S.; Morinaka, Y.; Iseki, K.; Sakurai, H. EP 208874, 1987.

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