Scandium(III)-Catalyzed Aza-Michael Addition of in Situ Generated ortho-Quinone Methides with Amines: An Efficient Access to Betti Base Derivatives

doi:10.6023/cjoc201808045

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 709-719.DOI: 10.6023/cjoc201808045 Previous Articles Next Articles

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Sc(Ⅲ)催化胺对邻亚甲基苯醌氮杂迈克尔加成反应合成贝蒂碱衍生物

张硕^a, 赵宁^a, 李庆刚^a, 张嘉祺^b, 侯梓桐^a, 刘一帆^a, 于一涛^a, 彭丹^a, 王峰^a, 李冰^a, 李金辉^a

a 齐鲁工业大学(山东省科学院) 山东省科学院新材料研究所山东省特种含硅新材料重点实验室济南 250014;
b 山东省实验中学济南 250001

收稿日期:2018-08-31 修回日期:2018-11-09 发布日期:2018-11-26
通讯作者: 张硕, 彭丹 E-mail:e50687e@163.com;lonarpeng@aliyun.com
基金资助:
山东省山东省科学院青年科学基金（No.2018QN0030）和国家自然科学基金（No.51503118）资助项目.

Scandium(III)-Catalyzed Aza-Michael Addition of in Situ Generated ortho-Quinone Methides with Amines: An Efficient Access to Betti Base Derivatives

Zhang Shuo^a, Zhao Ning^a, Li Qinggang^a, Zhang Jiaqi^b, Hou Zitong^a, Liu Yifan^a, Yu Yitao^a, Peng Dan^a, Wang Feng^a, Li Bing^a, Li Jinhui^a

a Shandong Provincial Key Laboratory for Special Silicone-Containing Materials, Advanced Materials Institute, Qilu University of Technology(Shandong Academy of Sciences), Jinan 250014;
b Shandong Experimental High School, Jinan 250001

Received:2018-08-31 Revised:2018-11-09 Published:2018-11-26
Contact: 10.6023/cjoc201808045 E-mail:e50687e@163.com;lonarpeng@aliyun.com
Supported by:
Project supported by the Shandong Provincial Natural Science Foundation (No. ZR2017BB033), the Youth Science Funds of Shandong Academy of Sciences (No. 2018QN0030) and the National Natural Science Foundation of China (No. 51503118).

1. Scandium(III)-Catalyzed Aza-Michael Addition of in Situ Generated ortho-Quinone Methides with Amines: An Efficient Access to Betti Base Derivatives.PDF(6196KB)

Abstract

o-Quinone derivatives are not only a variety of active and important intermediate, but also widely used in the synthesis of natural products and medicinal chemistry. In the present study, the Sc(Ⅲ) catalyzed aza-Michael addition to o-quinone methides by amines for the synthesis of Betti base derivatives was developed. The reaction was performed in a sealed tube at 90℃ for 4 h and the products were obtained in moderate to good yields (76%~96%).

Key words: o-quinone, Betti base, aza-Michael addtion, green chemistry

Cite this article

Zhang Shuo, Zhao Ning, Li Qinggang, Zhang Jiaqi, Hou Zitong, Liu Yifan, Yu Yitao, Peng Dan, Wang Feng, Li Bing, Li Jinhui. Scandium(III)-Catalyzed Aza-Michael Addition of in Situ Generated ortho-Quinone Methides with Amines: An Efficient Access to Betti Base Derivatives[J]. Chin. J. Org. Chem., 2019, 39(3): 709-719.

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[1] Betti, M. Org. Synth. 1929, 9, 60
[2] Waisser, K.; Gregor, K.; Kubicova, L.; Klimesova, V.; Kunes, J.; Machacek, M. Eur. J. Med. Chem. 2000, 35, 733.
[3] Bouaziz, Z.; Riondel, J.; Mey, A.; Berlion, M.; Villard, J.; Filliond, H. Eur. J. Med. Chem. 1991, 26, 469.
[4] Arthington, S. B.; Motley, A. M.; Warnock, D. W.; Morrison, C. J. J. Clin. Microbiol. 2000, 38, 2254.
[5] Chylinska, J. B.; Urbanski, T.; Mordarski, M. J. Med. Chem. 1963, 6, 484.
[6] Benameur, L.; Bouaziz, Z.; Nebois, P.; Bartoli, M. H.; Boitard, M.; Chem. Pharm. Bull. 1996, 44, 605.
[7] Mathew, B. P.; Kumar, A.; Sharma, S.; Shukla, P. K.; Nath, M. Eur. J. Med. Chem. 2010, 45, 1502.
[8] Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron. Lett. 2002, 43, 8367.
[9] Feng, J.; Bohle, D. S.; Li, C. J. Tetrahedron:Asymmetry 2007, 18, 1043.
[10] Kidwai, M.; Chauhan, R. Asian J. Org. Chem. 2013, 2, 395.
[11] Safari, J.; Zarnegar, Z. J. Mol. Catal. A:Chem. 2013, 379, 269.
[12] Hajjami, M.; Ghorbani, F.; Bakhti, F. Appl. Catal. A 2014, 470, 303.
[13] Hajipour, A. R.; Ghayeb, Y.; Sheikhan, N.; Ruoho, A. E. Tetrahedron Lett. 2009, 50, 5649.
[14] Pathak, T. P.; Sigman, M. S. J. Org. Chem. 2011, 76, 9210.
[15] Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18, 9160.
[16] Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.
[17] Wang, Z.; Sun, J. Synthesis 2015, 47, 3629.
[18] Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
[19] Kulikov, A.; Arumugam, S.; Popik, V. V. J. Org. Chem. 2008, 73, 7611.
[20] Mattson, A. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 4508
[21] Luan, Y.; Schaus, S. E. J. Am. Chem. Soc. 2012, 134, 19965.
[22] Shaikh, A. K.; Cobb, A. J. A.; Varounis, G. Org. Lett. 2012, 14, 584.
[23] Chen, M. W.; Gao, L. L.; Ye, Z. S.; Jiang, G. F.; Zhou, Y. G. Chem. Commun. 2013, 49, 1660.
[24] Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. A. Org. Lett. 2004, 6, 4049.
[25] Bai, W. J.; David, J. G.; Feng, Z. G.; Weaver, M. G.; Wu, K. L.; Pettus, T. R. R. Acc. Chem. Res. 2014, 47, 3655.
[26] Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.
[27] Liang, M.; Zhang, S.; Jia, J.; Tung, C.-H.; Wang, J.; Xu, Z. Org. Lett. 2017, 19, 2526.
[28] Zhao, W.; Wang, Z.; Chu, B.; Sun, J. Angew. Chem., Int. Ed. 2015, 54, 1910.
[29] Huang, Y.; Hayashi, T. J. Am. Chem. Soc. 2015, 137, 7556.
[30] Wang, Z.; Ai, F.; Wang, Z.; Zhao, W.; Zhu, G.; Lin, Z.; Sun, J. J. Am. Chem. Soc. 2015, 137, 383.
[31] Wu, B.; Yu, Z.; Gao, X.; Lan, Y.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2017, 56, 4006.
[32] Chen, P.; Wang, K. l; Guo, W.; Liu, X.; Liu, Y.; Li, C. Angew. Chem., Int. Ed. 2017, 56, 3689.
[33] Nising, C. F.; Brase, S. Chem. Soc. Rev. 2008, 37, 1218.
[34] Nising, C. F.; Brase, S. Chem. Soc. Rev. 2012, 41, 988.
[35] Heravi, M. M.; Hajiabbasi, P. Mol. Diversity 2014, 18, 411.
[36] Balasubramanian, K.; Selvaraj, S. Synthesis 1977, 767.
[37] Arct, J.; Jakubska, E.; Olszewska, G. Synthesis 1977, 314.
[38] Arct, J.; Jakubska, E.; Olszewska, G. Synth. Commun. 1978, 8, 143.
[39] Samarakoon, T. B.; Hur, M. Y.; Kurtz, R. D.; Hanson, P. R. Org. Lett. 2010, 12, 2182.
[40] Osyanin, V. A.; Nakushnov, V. Y.; Osipov, D. V.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2010, 46, 1027.
[41] Osyanin, V. A.; Osipov, D. V.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2010, 46, 377.
[42] Osyanin, V. A.; Nakushnov, V. Y.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2011, 47, 755.
[43] Osyanin, V. A.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2009, 45, 833.
[44] Sidorina, N. E.; Osyanin, V. A. Chem. Heterocycl. Compd. 2005, 41, 1201.
[45] Sidorina, N. E.; Osyanin, V. A. Chem. Heterocycl. Compd. 2007, 43, 1065
[46] Wang, P.; Song, Y.; Zhang, L.; He, H.; Zhou, X. Curr. Med. Chem. 2005, 12, 2893.
[47] Freccero, M. Mini-Rev. Org. Chem. 2004, 1, 403.
[48] Zhang, S.; Peng, D.; Zhao, N.; Yu, Y.; Wang, F.; Liu, H.; Yi, G. Chin. J. Org. Chem. 2019, 39, 555(in Chinese). (张硕, 彭丹, 赵宁, 于一涛, 王峰, 刘海龙, 伊港, 有机化学, 2019, 39, 555.)
[49] Zhen, M. M.; Zhang, D. F.; Zhang, Z. Y.; Peng, Y. Q. ACS Comb. Sci. 2016, 18, 697.
[50] Erb, W.; Albini, M.; Rouden, J.; Blanchet, J. J. Org. Chem. 2014, 79, 10568.
[51] Katritzky, A. R.; Abdel-Fattah, A. A. A.; Tymoshenko, D. O.; Belyakov, S. A.; Ghiviriga, I.; Steel, P. J. J. Org. Chem. 1999, 64, 6071.

Sc(Ⅲ)催化胺对邻亚甲基苯醌氮杂迈克尔加成反应合成贝蒂碱衍生物

Scandium(III)-Catalyzed Aza-Michael Addition of in Situ Generated ortho-Quinone Methides with Amines: An Efficient Access to Betti Base Derivatives

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