Citation: 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. doi: 10.6023/cjoc201910038 shu

"On Water" Nucleophilic Addition of Pyrazolones to Trifluoromethyl Ketones

Key Laboratory of Organo-pharmaceutical Chemistry, Gannan Normal University, Ganzhou, Jiangxi 341000

Corresponding author: Zhang Yong, yong_zhanggnnu@126.com
Received Date: 29 October 2019
Revised Date: 14 January 2020
Available Online: 14 February 2020
Fund Project: the Education Department of Jiangxi Province GJJ170835the Jiangxi Provincial Department of Science and Technology Fund 20144BAB2130003Project supported by the National Natural Science Foundation of China (No. 21562003), the Jiangxi Provincial Department of Science and Technology Fund (20192BAB213007 and 20144BAB2130003), and the Education Department of Jiangxi Province (No. GJJ170835)the Jiangxi Provincial Department of Science and Technology Fund 20192BAB213007the National Natural Science Foundation of China 21562003

Figures(2)

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.
- "on water" reaction,
- nucleophilic addition,
- pyrazolone,
- trifluoromethyl ketone
1. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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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