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有机化学 2015

碳酸铯催化吡唑与α,β-不饱和酮的氮杂Michael反应有机化学

DOI: 10.6023/cjoc201406051, PP. 121-128

杨靖亚, 马奔, 周红艳, 占宝华, 李政

Keywords: Michael加成,含氮杂环,α,β-不饱和酮,催化,碳酸铯

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Abstract:

发展了一种碳酸铯催化吡唑与α,β-不饱和酮的氮杂Michael反应新方法.在5mol%Cs2CO3存在下,于1,4-二氧六环中回流反应7～12h,以86%～95%的产率得到21种β-(N1-吡唑基)酮.此法对芳香类和脂肪类α,β-不饱和酮均适用良好,易实现克级放大.产物可容易地转化为相应的γ-氨基醇.发展的方法同样适用于吡唑与丙烯酸甲酯和硝基苯乙烯的氮杂Michael反应.

References

[1]	(a) Giornal, F.; Pazenok, S.; Rodefeld, L.; Lui, N.; Vors, J.-P.; Leroux, F. R. J. Fluorine Chem. 2013, 152, 2. (b) Lamberth, C. Heterocycles 2007, 71, 1467.
[2]	Raju, H.; Chandrappa, S.; Prasanna, D. S.; Ananda, H.; Nagamani, T. S.; Byregowda, S. M.; Rangappa, K. S. Recent Pat. Anti-Cancer Drug Discovery 2011, 6, 186.
[3]	Bekhit, A. A.; Hymete, A.; Bekhit, A. E. A.; Damtew, A.; Aboul-Enein, H. Y. Mini-Rev. Med. Chem. 2010, 10, 1014.
[4]	Secci, D.; Bolasco, A.; Chimenti, P.; Carradori, S. Curr. Med. Chem. 2011, 18, 5114.
[5]	Kumar, G. G.; Vikas, K.; Vinod, K. Res. J. Chem. Environ. 2011, 15, 90.
[6]	Peng, X.-M.; Cai, G.-X.; Zhou, C.-H. Curr. Top. Med. Chem. 2013, 13, 1963.
[7]	(a) Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. Chem. Rev. 2011, 111, 6984. (b) Fustero, S.; Simón-Fuentes, A.; Sanz-Cervera, J. F. Org. Prep. Proced. Int. 2009, 41, 253.
[8]	(a) Amara, Z.; Caron, J.; Joseph, D. Nat. Prod. Rep. 2013, 30, 1211. (b) Lin, D.; Wang, J.; Liu, H. Chin. J. Org. Chem. 2013, 33, 2098 (in Chinese). (林岱宗, 王江, 柳红, 有机化学, 2013, 33, 2098.) (c) Weiner, B.; Szymański, W.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L. Chem. Soc. Rev. 2010, 39, 1656. (d) Mikami, K.; Fustero, S.; Sánchez-Roselló, M.; Ace？a, J. L.; Soloshonok, V.; Sorochinsky, A. Synthesis 2011, 3045. (e) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117.
[9]	For selected reviews on aza-Michael reaction, see: (a) Wang, J.; Li, P.; Choy, P. Y.; Chan, A. S. C.; Kwong, F. Y. ChemCatChem 2012, 4, 917. (b) Enders, D.; Wang, C.; Liebich, J. X. Chem. Eur. J. 2009, 15, 11058. (c) Xu, L.-W.; Xia, C.-G. Eur. J. Org. Chem. 2005, 633. (d) Xu, L.-W.; Xia, C.-G.; Wu, H.; Yang, L.; Zhou, W.; Zhang, Y. Chin. J. Org. Chem. 2005, 25, 167 (in Chinese). (徐利文, 夏春谷, 吴乎格吉乐土, 杨磊, 周伟, 张妍, 有机化学, 2005, 25, 167.)
[10]	(a) Gandelman, M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 2393. (b) Wang, J.; Li, H.; Zu, L.; Wang, W. Org. Lett. 2006, 8, 1391. (c) Dinér, P.; Nielsen, M.; Marigo, M.; J？rgensen, K. A. Angew. Chem. Int. Ed. 2007, 46, 1983. (d) Uria, U.; Vicario, J. L.; Badía, D.; Carrillo, L. Chem. Commun. 2007, 2509. (e) Liu, B. K.; Wu, Q.; Qian, X. Q.; Lv, D. S.; Lin, X. F. Synthesis 2007, 2653. (f) Wang, J.; Zu, L.; Li, H.; Xie, H.; Wang, W. Synthesis 2007, 2576. (g) Lin, Q.; Meloni, D.; Pan, Y.; Xia, M.; Rodgers, J.; Shepard, S.; Li, M.; Galya, L.; Metcalf, B.; Yue, T.-Y.; Liu, P.; Zhou, J. Org. Lett. 2009, 11, 1999. (h) Luo, G. S.; Zhang, S. L.; Duan, W. H.; Wang, W. Synthesis 2009, 1564. (i) Lv, J.; Wu, H.; Wang, Y. Eur. J. Org. Chem. 2010, 2073. (j) Zhou, Y.; Li, X.; Li, W.; Wu, C.; Liang, X.; Ye, J. Synlett 2010, 2357. (k) Hou, X.; Hemit, H.; Yong, J.; Nie, L.; Aisa, H. A. Synth. Commun. 2010, 40, 973. (l) Guo, H.-M.; Yuan, T.-F.; Niu, H.-Y.; Liu, J.-Y.; Mao, R.-Z.; Li, D.-Y.; Qu, G.-R. Chem. Eur. J. 2011, 17, 4095. (m) Lee, S.-J.; Youn, S.-H.; Cho, C.-W. Org. Biomol. Chem. 2011, 9, 7734. (n) Li, H.; Zhao, J.; Zeng, L.; Hu, W. J. Org. Chem. 2011, 76, 8064. (o) Uria, U.; Reyes, E. m.; Vicario, J. L.; Badía, D.; Carrillo, L. Org. Lett2015-1-28. 2011, 13, 336. (p) Wang, J.; Wang, W.; Liu, X.; Hou, Z.; Lin, L.; Feng, X. Eur. J. Org. Chem. 2011, 2039. (q) Wu, H.; Tian, Z.; Zhang, L.; Huang, Y.; Wang, Y. Adv. Synth. Catal. 2012, 354, 2977.
[11]	Qian, C.; Xu, J.-M.; Wu, Q.; Lv, D.-S.; Lin, X.-F. Tetrahedron Lett. 2007, 48, 6100.
[12]	Xu, J.-M.; Qian, C.; Liu, B.-K.; Wu, Q.; Lin, X.-F. Tetrahedron 2007, 63, 986.
[13]	Wang, J.; Li, P.-F.; Chan, S. H.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2012, 53, 2887.
[14]	Wu, Y.-J. Tetrahedron Lett. 2006, 47, 8459.
[15]	Uddin, M. I.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2008, 1402.
[16]	Lee, I. Y. C.; Lee, K. C.; Lee, H. W. Bull. Korean Chem. Soc. 2012, 33, 3535.
[17]	Bhanuchandra, M.; Kuram, M. R.; Sahoo, A. K. Org. Biomol. Chem. 2012, 10, 3538.
[18]	During preparation of this manuscript, an organocatalytic asymmetric aza-Michael addition of pyrazole to chalcone was developed. See: Li, P.; Fang, F.; Chen, J.; Wang, J. Tetrahedron: Asymmetry 2014, 25, 98.
[19]	(a) Lehmann, F. Synlett 2004, 2447. (b) Duan, X.-F.; Zhang, Z.-B. Chin. J. Org. Chem. 2006, 26, 573 (in Chinese). (段新方, 张站斌, 有机化学, 2006, 26, 573.)
[20]	(a) Liu, D.; Gao, W.; Wang, C.; Zhang, X. Angew. Chem., Int. Ed. 2005, 44, 1687. (b) Calow, A. D. J.; Batsanov, A. S.; Fernández, E.; Solé, C.; Whiting, A. Chem. Commun. 2012, 48, 11401.
[21]	Wu, Y.; Wang, J.; Li, P.; Kwong, F. Y. Synlett 2012, 788.
[22]	(a) Kawatsura, M.; Aburatani, S.; Uenishi, J. Tetrahedron 2007, 63, 4172. (b) Aburatani, S.; Kawatsura, M.; Uenishi, J. Heterocycles 2007, 71, 189.

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