研究论文

“水上”吡唑啉酮与三氟甲基酮的亲核加成

  • 罗亮 ,
  • 曹晓梅 ,
  • 赖国伟 ,
  • 刘金香 ,
  • 罗海清 ,
  • 路东亮 ,
  • 张勇
展开
  • 赣南师范大学有机药物化学重点实验室 江西赣州 341000

收稿日期: 2019-10-29

  修回日期: 2020-01-14

  网络出版日期: 2020-02-15

基金资助

国家自然科学基金(No.21562003)、江西省科学技术厅基金(Nos.20192BAB213007和20144BAB2130003)和江西省教育厅(No.GJJ170835)资助项目.

“On Water” Nucleophilic Addition of Pyrazolones to Trifluoromethyl Ketones

  • Luo Liang ,
  • Cao Xiaomei ,
  • Lai Guowei ,
  • Liu Jinxiang ,
  • Luo Haiqing ,
  • Lu Dongliang ,
  • Zhang Yong
Expand
  • Key Laboratory of Organo-pharmaceutical Chemistry, Gannan Normal University, Ganzhou, Jiangxi 341000

Received date: 2019-10-29

  Revised date: 2020-01-14

  Online published: 2020-02-15

Supported by

Project 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).

摘要

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.

本文引用格式

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 . DOI: 10.6023/cjoc201910038

Abstract

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.

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.
文章导航

/