Preparation of 1,3,5-Trisubstituted Pyrazoles with Cascade Reaction Catalyzed by Cu between Hydrazonoyl Halide and Terminal Alkynes

doi:10.6023/cjoc201511033

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1127-1132.DOI: 10.6023/cjoc201511033 Previous Articles Next Articles

NOTE

铜催化腙酰卤与端炔的串联反应制备1,3,5-三取代吡唑衍生物

李福卫, 王小龙, 于海涛

南京中医药大学药学院南京 210032

收稿日期:2015-11-18 修回日期:2015-12-22 发布日期:2016-01-07
通讯作者: 于海涛 E-mail:njubilly@foxmail.com
基金资助:
国家自然科学基金(No.81302650)资助项目.

Preparation of 1,3,5-Trisubstituted Pyrazoles with Cascade Reaction Catalyzed by Cu between Hydrazonoyl Halide and Terminal Alkynes

Li Fuwei, Wang Xiaolong, Yu Haitao

Nanjing University of Chinese Medicine, School of Pharmacy, Nanjing 210023

Received:2015-11-18 Revised:2015-12-22 Published:2016-01-07
Supported by:
Project supported by the National Natural Science Foundation of China (No. 81302650).

1. Preparation of 1,3,5-Trisubstituted Pyrazoles with Cascade Reaction Catalyzed by Cu between Hydrazonoyl Halide and Terminal Alkynes.PDF(3964KB)

Abstract

Cascade reaction, including nucleophilic substitution and addition cyclization, catalyzed by Cu⁺ salt between substituted aryl hydrazonoyl halides and terminal alkynes could produce 1,3,5-trisubstituted pyrazoles. The method employed easily available aryl hydrazonoyl halide and terminal alkynes as starting materials under 45 ℃ in green acetonitrile/water solvent, regioselectively generating 1,3,5-trisubstituted pyrazoles in high yield. Above all, functional groups containing active hydrogen would not disturb this reaction, example for carboxyl and hydroxyl. In this work 17 pyrazole derivatives with different substituent group were achieved by this method. So it could be a general method to synthesize 1,3,5-trisubstituted pyrazoles.

Key words: 1,3,5-trisubstituted pyrazole, hydrazonoyl halide, terminal alkyne, Cascade reaction

Cite this article

Li Fuwei, Wang Xiaolong, Yu Haitao. Preparation of 1,3,5-Trisubstituted Pyrazoles with Cascade Reaction Catalyzed by Cu between Hydrazonoyl Halide and Terminal Alkynes[J]. Chin. J. Org. Chem., 2016, 36(5): 1127-1132.

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[1] (a) Elguero, J.; Pilar, J.; Nadine, S.; Artur, M. S. Targets Heterocycl. Syst. 2002, 6, 52.
(b) Bondock, S.; Fadaly, W.; Metwally, M. A. Eur. J. Med. Chem. 2010, 45, 3692.
(c) Barsoum, F. F.; Girgis, A. S. Eur. J. Med. Chem. 2009, 44, 2172.
(d) Manfredini, S.; Bazzanini, R.; Baraldi, P. G.; Guarneri, M. J. Med. Chem. 1992, 35, 917.
[2] (a) Rudorf, W. D.; Augustin, M. J. Prakt. Chem. 1978, 320, 585.
(b) Battistone, M. J.; Sawitzke, A. D. Clin. Med. Insights: Ther. 2010, 2, 245.
[3] Akula, R.; Suresh, B. M.; Ramamohan, M.; Raghavendra, K. R.; Thalishetti, K,; Gangadhara, R. C.; Vaikunta, L. R. Tetrahedron Lett. 2014, 55, 2986.
[4] (a) Rosa, F. A.; Machado, P.; Vargas, P. S.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P. Synlett 2008, 1673.
(b) Giacomelli, G.; Porcheddu, A.; Salaris, M.; Taddei, M. Eur. J. Org. Chem. 2003, 537.
(c) Donnohue, B. A.; Michelotti, E. L.; Reader, J. C.; Reader, V.; Stirling, M.; Tice, C. N. J. Comb. Chem. 2002, 4, 23.
[5] (a) Clovis, J. S.; Fliege, W.; Huisgen, R. Chem. Ber. 1983, 116, 3062.
(b) Huisgen, R.; Seidel, M.; Wallbillich, G. Tetrahedron1962, 17, 3.
(c) Fliege, W.; Grashey, R.; Huisgen, R. Chem. Ber. 1984, 117, 1194.
[6] (a) Liang, D. D.; Zhu, Q. Asian J. Org. Chem. 2015, 4, 42.
(b) Li, X.; He, L.; Jiang, H. J. Org. Chem. 2013, 78, 3636.
(c) Hu, J.; Chen, S.; Sun, Y.; Yang, J.; Rao, Y. Org. Lett. 2012, 14, 5030.
(d) Zhang, T.; Bao, W. J. Org. Chem. 2013, 78, 1317.
[7] Browne, D. L.; Taylor, J. B.; Plant, A.; Harrity, J. P. A. J. Org. Chem. 2010, 75, 984.
[8] Ahmed, M. S. M.; Kobayashi, K.; Mori, A. Org. Lett. 2005, 7, 4487.
[9] (a) Longhi, K.; Moreira, D. N.; Marzari, M. R. B.; Floss, V. M.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P. Tetrahedron Lett. 2010, 51, 3193.
(b) Bhat, B. A.; Puri, S. C.; Qurishi, M. A.; Dhar, K. L.; Qazi, G. N. Synth. Commun. 2005, 35, 1135.
[10] Zara, M.; Kivrak, A. J. Org. Chem. 2011, 76, 9379.
[11] Sun, A. X.; Ye, J. H.; Yu, H. T.; Zhang, W. C.; Wang, X. L. Tetrahedron Lett. 2014, 55, 889.
[12] (a) Rostovtsev, V.; Green, L.; Fokin, V.; Sharpless, K. Angew. Chem., Int. Ed. 2002, 41, 2596.
(b) Tornoe, C.; Christensen, C.; Meldel, M. J. Org. Chem. 2002, 67, 3057.
(c) Brik, A.; Muldoon, J.; Lin, Y.; Elder, J. ChemBioChem 2003, 4, 1246.
(d) Chan, T. R.; Hilgraf, R.; Shapless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853.
(e) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Shapless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192.
[13] (a) Faucher, N. E.; Martres, P. WO 2005049578, 2005 [Chem. Abstr. 2005, 143, 26597].
(b) Silvestri, R.; Cascio, M. G.; Giuseppe, L. R.; Piscitelli, F.; Lavecchia, A.; Brizzi, A.; Pasquini, S.; Botta, M.; Novellino, E.; Vincenzo, D. M.; Corelli, F. J. Org. Chem. 2008, 51, 1560.

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铜催化腙酰卤与端炔的串联反应制备1,3,5-三取代吡唑衍生物

Preparation of 1,3,5-Trisubstituted Pyrazoles with Cascade Reaction Catalyzed by Cu between Hydrazonoyl Halide and Terminal Alkynes

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