铜试剂介导下烯胺酮的氧化环化/迁移合成取代的2H-氮杂丙烯啶的方法
收稿日期: 2016-11-22
修回日期: 2016-12-08
网络出版日期: 2016-12-29
基金资助
河南科技大学博士科研启动（No.4008-13480042）资助项目.
Copper-Promoted Oxidative Cyclization/Migration of Enaminone for Synthesis of Functionalized 2H-Azirines
Received date: 2016-11-22
Revised date: 2016-12-08
Online published: 2016-12-29
Supported by
Project supported by the Students Research Training Program of Henan University of Science and Technology (No. 4008-13480042).
杨坤 , 段希焱 , 李军波 , 刘普 , 郭旭明 , 李军 , 周惠云 , 刘宁 , 刘建伟 , 王双双 , 李绘闲 , 杜亚珍 , 马军营 . 铜试剂介导下烯胺酮的氧化环化/迁移合成取代的2H-氮杂丙烯啶的方法[J]. 有机化学, 2017 , 37(4) : 1040 -1045 . DOI: 10.6023/cjoc201611025
A new method for the synthesis of 2-benzoylated 2H-azirine via Cu-promoted oxidative cyclization/migration of enaminone was reported. The advantage of our approach is mild reaction condition, short reaction time and easy operation.
Key words： copper-promoted; 2H-azirines; enaminone; oxidative cyclization/migration
[1] (a) Singh, R.; Kissling, R. M.; Letellier, M.-A.; Nolan, S. P. Tsang, W. C. P.; Zheng, N.; Buchwald S. L. J. Am. Chem. Soc. 2005, 127, 14560.
(b) Brown, E. G. Ring Nitrogen and Key Biomolecules, Kluwer, Boston, MA, 1998.
(c) Li, J.-J.; Corey, E. J. Name Reactions in Heterocyclic Chemistry, Wiley-Interscience, Hoboken, NJ, 2005.
[2] Sun, X.; Lyu, Y.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Org. Lett. 2013, 15, 6222.
[3] For selected examples, see: (a) Xin, Z.; Gøgsig, T. M.; Lindhardt, A. T.; Skrydstrup, T. Org. Lett. 2012, 14, 284.
(b) Nahmany, M.; Melman, A. Org. Lett. 2001, 3, 3733.
(c) Kim, S.; Lee, J. I. J. Org. Chem. 1984, 49, 1712.
(d) Masamune, S.; Hayase, Y.; Schilling, W.; Chan, W. K.; Bates, G. S. J. Am. Chem. Soc. 1977, 99, 6756.
(e) Takimoto, S.; Inanaga, J.; Katsuki, T.; Yamagughi, M. Bull. Chem. Soc. Jpn. 1976, 49, 2335.
(f) Rossi, R. A.; de Rossi, R. H. J. Org. Chem. 1974, 39, 855.
(g) Kaiser, E. M.; Woodruff, R. A. J. Org. Chem. 1970, 35, 1198.
(h) Parish, R. C.; Stock, L. M. J. Org. Chem. 1965, 30, 927.
(i) Zhu, Y.; Wei, Y. RSC Adv. 2013, 3, 13668.
(j) Zhang, H.; Shi, R.; Ding, A.; Lu, L.; Chen, B.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 12542.
(k) Li, X.; Zou, D.; Zhu, H.; Wang, Y.; Li, J.; Wu, Y.; Wu, Y. Org. Lett. 2014, 16, 1836.
(l) Katritzky, A. R.; Wang, M.; Wilkerson, C. R.; Yang, H. J. Org. Chem. 2003, 68, 9105.
(m) Alonso-Cruz, C. R.; Kennedy, A. R.; Rodríguez, M. S.; Suárez, E. J. Org. Chem. 2008, 73, 4116.
[4] (a) Jin, L.; Wu, Y.; Zhao, X. J. Org. Chem. 2015, 80, 3547.
(b) Loy, N. S. Y.; Singh, A.; Xu, X.; Park, C.-M. Angew. Chem., Int. Ed. 2013, 52, 2212.
(c) Prechter, A.; Henrion, G.; Bel, P. F.; Gagosz, F. Angew. Chem., Int. Ed. 2014, 53, 4959.
(d) Candito, D. A.; Lautens, M. Org. Lett. 2010, 12, 3312.
(e) Jana, S.; Clements, M. D.; Sharp, B. K.; Zheng, N. Org. Lett. 2010, 12, 3736.
(f) Zhu, L.; Yu, Y.; Mao, Z.; Huang, X. Org. Lett. 2015, 17, 30.
(g) Liu, X.; Cheng, R.; Zhao, F.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Org. Lett. 2012, 14, 5480.
(h) Loy, N. S. Y.; Kim, S.; Park, C.-M. Org. Lett. 2015, 17, 395.
[5] (a) Katritzky, A. R.; Wang, M.; Wilkerson, C. R.; Yang, H. J. Org. Chem. 2003, 68, 9105.
(b) Alonso-Cruz, C. R.; Kennedy, A. R.; Rodríguez, M. S.; Suárez, E. J. Org. Chem. 2008, 73, 4116.
(c) Alonso-Cruz, C. R.; Kennedy, A. R.; Rodríguez, M. S.; Suárez, E. Org. Lett. 2003, 5, 3729.
(d) Knoll, W.; Mieusset, J.-L.; Arion, V. B.; Brecker, L.; Brinker, U. H.; Org. Lett. 2010, 12, 2366.
(e) Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651.
(f) Moerdyk, J. P.; Bielawski, C. W. J. Am. Chem. Soc. 2012, 134, 6116.
(g) Duan X.; Yang, K.; Liu, J.; Kong, X.; Liang, J.; Zhou, D.; Zhou, H.; Zhang, Y.; Liu, N.; Feng, S.; Gu, G.; Lu, J.; Song, N.; Zhang, D.; Ma J. Adv. Synth. Catal. 2016, 358, 3161.
[6] (a) Palacios, F.; Ochoa de Retana, A. M.; Martinez de Marigorta, E.; Manuel de los Santos, J. Org. Prep. Proced. Int. 2002, 34, 219.
(b) Palacios, F.; Ochoa de Retana, A. M.; Martinez de Marigorta, E.; Manuel de los Santos, J. Eur. J. Org. Chem. 2001, 13, 2401.
(c) Melo, P.; Rocha G. Curr. Org. Chem. 2004, 1, 275.
(d) Katritzky, A. R.; Wang, M.; Wilkerson, C. R.; Yang, H. J. Org. Chem. 2003, 68, 9105.
(e) Hassner A.; Alexanian V. J. Org. Chem. 1979, 44, 3861.
(f) Atkinson R. S.; Kelly B. J. J. Chem. Soc., Chem. Commun. 1989, 836.
(g) Nunes, C. M.; Reva, I.; Pinho e Melo, T. M. V. D.; Fausto, R. J. Org. Chem. 2012, 77, 8723.
(h) Leonard, N. J.; Zwanenburg B. J. Am. Chem. Soc. 1967, 89, 4456.
[7] Li, X.; Du, Y.; Liang, Z.; Li, X.; Pan, Y.; Zhao, K. Org. Lett. 2009, 11, 2643.
[8] Duan, X.; Kong, X.; Zhao, X.; Yang, K.; Zhou, H.; Zhou, D.; Zhang, Y.; Liu, J.; Ma, J.; Liu, N.; Wang, Z. Tetrahedron Lett. 2016, 57, 1446.
[9] (a) Wang, J.; Liu, C.; Yuan, J.; Lei A. Angew. Chem., Int. Ed. 2013, 52, 2256.
(b) Rout, S. K.; Guin, S.; Ali, W.; Gogoi, A.; Patel, B. K. Org. Lett. 2014, 16, 3086.
[10] (a) Yuan, Y.; Ji, X.; Zhao, D. Eur. J. Org. Chem. 2010, 5274.
(b) Stepovik, L. P.; Gulenova, M. V.; Kalacheva, I. A.; Potkina, A. Y. Russ. J. Gen. Chem. 2011, 81, 550.
/
| 〈 |
|
〉 |
