Copper-Promoted Oxidative Cyclization/Migration of Enaminone for Synthesis of Functionalized 2H-Azirines

doi:10.6023/cjoc201611025

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 1040-1045.DOI: 10.6023/cjoc201611025 Previous Articles Next Articles

Notes

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

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

河南科技大学化工与制药学院洛阳 471023

收稿日期:2016-11-22 修回日期:2016-12-08 发布日期:2016-12-29
通讯作者: 段希焱, 马军营 E-mail:duanxiyan@tju.edu.cn;majy379@haust.edu.cn
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

Yang Kun, Duan Xiyan, Li Junbo, Liu Pu, Guo Xuming, Li Jun, Zhou Huiyun, Liu Ning, Liu Jianwei, Wang Shuangshuang, Li Huixian, Du Yazhen, Ma Junying

School of Chemical Engineering & Pharmaceutics, Henan University of Science and Technology, Luoyang 471023

Received:2016-11-22 Revised:2016-12-08 Published:2016-12-29
Contact: 10.6023/cjoc201611025 E-mail:duanxiyan@tju.edu.cn;majy379@haust.edu.cn
Supported by:
Project supported by the Students Research Training Program of Henan University of Science and Technology (No. 4008-13480042).

1. Copper-Promoted Oxidative Cyclization/Migration of Enaminone for Synthesis of Functionalized 2H-Azirines.PDF(662KB)

Abstract

Cite this article

Yang Kun, Duan Xiyan, Li Junbo, Liu Pu, Guo Xuming, Li Jun, Zhou Huiyun, Liu Ning, Liu Jianwei, Wang Shuangshuang, Li Huixian, Du Yazhen, Ma Junying. Copper-Promoted Oxidative Cyclization/Migration of Enaminone for Synthesis of Functionalized 2H-Azirines[J]. Chin. J. Org. Chem., 2017, 37(4): 1040-1045.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

[1]	Ning Liu, Xiaodan Cuan, Hui Li, Xiyan Duan. Progress in the Study of α-Functionalization of Enaminone [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 602-621.
[2]	Keying Du, Zhanming Zhang, Weijian Sheng. Copper-Catalyzed the Synthesis of 3-Trifluoromethylchromone via Trifluoromethyl Radical Addition Tandem Cyclization Reaction of 2-Hydroxyphenyl Enaminones [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3242-3248.
[3]	Yu Zhao, Zhuo Chen, Xuebing Chen. Synthesis of 2-Quinolinone Derivatives via [3+3] Cyclization Promoted by Acetic Anhydride [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 731-737.
[4]	Xiaobiao Lu, Xi Xiao, Ming Zhang, Changfeng Wan, Haoqing Hou, Jieping Wan. Highly Selective Synthesis of 2-Substituted Pyrido[2,3-b]indole Derivatives Catalyzed by Iron Salts [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4444-4449.
[5]	Guo Yuanyuan, Liu Zhenwei, Zhu Mingxiang, Li Linlin, Li Jingya, Zou Dapeng, Wu Yusheng, Wu Yangjie. Copper-Promoted Dimethylthiolation of Benzamides under Assistance of 8-Aminoquinoline Group [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 724-730.
[6]	Wang Guodong, Guo Yanhui, Wan Jieping. Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH₂-Amidines [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 645-650.
[7]	Wang Zhanlin, Li Ruyi, Qian Huimin, Yao Changsheng. Effect of Temperature on N-Heterocyclic Carbene-Catalyzed[3+3] Annulation of α-Bromoenal with Enaminone [J]. Chin. J. Org. Chem., 2019, 39(7): 2075-2083.
[8]	Zhao Yu, Tang Bo, Liu Xinlei, Li Wanzhen, Huang Mingyi, Wang Ming'an. Regioselective Preparation of Enaminone via Enol Methyl Ether of 3-Acetyl-2-butenolide and Different Amines [J]. Chin. J. Org. Chem., 2017, 37(4): 975-986.
[9]	Chen Xuebing, Bai Hairui, Huang Chao. Concise Synthesis of Quinolinone Derivatives [J]. Chin. J. Org. Chem., 2017, 37(4): 881-888.
[10]	Liu Ning, Duan Xiyan, Zhou Huiyun. Study of the Substitution Reaction between 2H-Azirines and 1H-Benzotriazole [J]. Chin. J. Org. Chem., 2017, 37(12): 3236-3241.
[11]	Lu Lingling, Xu Hui, Zhou Pan, Yu Fuchao. Progress in Synthesis of 1,4-Dihydropyridines [J]. Chinese Journal of Organic Chemistry, 2016, 36(12): 2858-2879.
[12]	Wei Zhenzhong, Xiao Lan, Wang Yongqiu, Li Pinhua. Green Synthesis of Enaminones Catalyzed by ZSM-5 [J]. Chin. J. Org. Chem., 2014, 34(5): 985-988.
[13]	Qu Yiping, Wang Longxiang, Zhou Xiaoyu, Feng Xiujuan, Bao Ming. Copper-Catalyzed Condensation Reaction of Amines with 1,3-Dicarbonyl Compounds to Produce Enaminones [J]. Chin. J. Org. Chem., 2013, 33(04): 860-865.
[14]	CHEN Yan*^,a,TU Shu-Jiang^b,JIANG Bo^b,LI Chun-Mei^b. Three-Component One-Pot Synthesis of 1-Carboxymethy-6-aryl-1,2,3,4,5,6-hexahydroindeno[2,3-b]quinoline-5,11–dione [J]. Chin. J. Org. Chem., 2007, 27(10): 1288-1291.
[15]	LI Ming*^,a,GUO Wei-Si^a,WEN Li-Rong^a,YANG Hua-Zheng^b. Synthesis of Enaminones and Their Utility in Organic Synthesis [J]. Chin. J. Org. Chem., 2006, 26(9): 1192-1207.

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

Copper-Promoted Oxidative Cyclization/Migration of Enaminone for Synthesis of Functionalized 2H-Azirines

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments