Chinese Journal of Organic Chemistry >
Scandium(III)-Catalyzed Aza-Michael Addition of in Situ Generated ortho-Quinone Methides with Amines: An Efficient Access to Betti Base Derivatives
Received date: 2018-08-31
Revised date: 2018-11-09
Online published: 2018-11-26
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).
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
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]. Chinese Journal of Organic Chemistry, 2019 , 39(3) : 709 -719 . DOI: 10.6023/cjoc201808045
[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.
/
| 〈 |
|
〉 |
