Source: http://sioc-journal.cn/Jwk_yjhx/EN/abstract/abstract346884.shtml
Timestamp: 2019-04-23 00:36:06+00:00

Document:
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%).
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).
Zhang Shuo,Zhao Ning,Li Qinggang等. 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.
 Waisser, K.; Gregor, K.; Kubicova, L.; Klimesova, V.; Kunes, J.; Machacek, M. Eur. J. Med. Chem. 2000, 35, 733.
 Bouaziz, Z.; Riondel, J.; Mey, A.; Berlion, M.; Villard, J.; Filliond, H. Eur. J. Med. Chem. 1991, 26, 469.
 Arthington, S. B.; Motley, A. M.; Warnock, D. W.; Morrison, C. J. J. Clin. Microbiol. 2000, 38, 2254.
 Chylinska, J. B.; Urbanski, T.; Mordarski, M. J. Med. Chem. 1963, 6, 484.
 Benameur, L.; Bouaziz, Z.; Nebois, P.; Bartoli, M. H.; Boitard, M.; Chem. Pharm. Bull. 1996, 44, 605.
 Mathew, B. P.; Kumar, A.; Sharma, S.; Shukla, P. K.; Nath, M. Eur. J. Med. Chem. 2010, 45, 1502.
 Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron. Lett. 2002, 43, 8367.
 Feng, J.; Bohle, D. S.; Li, C. J. Tetrahedron:Asymmetry 2007, 18, 1043.
 Kidwai, M.; Chauhan, R. Asian J. Org. Chem. 2013, 2, 395.
 Safari, J.; Zarnegar, Z. J. Mol. Catal. A:Chem. 2013, 379, 269.
 Hajjami, M.; Ghorbani, F.; Bakhti, F. Appl. Catal. A 2014, 470, 303.
 Hajipour, A. R.; Ghayeb, Y.; Sheikhan, N.; Ruoho, A. E. Tetrahedron Lett. 2009, 50, 5649.
 Pathak, T. P.; Sigman, M. S. J. Org. Chem. 2011, 76, 9210.
 Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18, 9160.
 Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.
 Wang, Z.; Sun, J. Synthesis 2015, 47, 3629.
 Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
 Kulikov, A.; Arumugam, S.; Popik, V. V. J. Org. Chem. 2008, 73, 7611.
 Luan, Y.; Schaus, S. E. J. Am. Chem. Soc. 2012, 134, 19965.
 Shaikh, A. K.; Cobb, A. J. A.; Varounis, G. Org. Lett. 2012, 14, 584.
 Chen, M. W.; Gao, L. L.; Ye, Z. S.; Jiang, G. F.; Zhou, Y. G. Chem. Commun. 2013, 49, 1660.
 Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. A. Org. Lett. 2004, 6, 4049.
 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.
 Liang, M.; Zhang, S.; Jia, J.; Tung, C.-H.; Wang, J.; Xu, Z. Org. Lett. 2017, 19, 2526.
 Zhao, W.; Wang, Z.; Chu, B.; Sun, J. Angew. Chem., Int. Ed. 2015, 54, 1910.
 Huang, Y.; Hayashi, T. J. Am. Chem. Soc. 2015, 137, 7556.
 Wang, Z.; Ai, F.; Wang, Z.; Zhao, W.; Zhu, G.; Lin, Z.; Sun, J. J. Am. Chem. Soc. 2015, 137, 383.
 Wu, B.; Yu, Z.; Gao, X.; Lan, Y.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2017, 56, 4006.
 Chen, P.; Wang, K. l; Guo, W.; Liu, X.; Liu, Y.; Li, C. Angew. Chem., Int. Ed. 2017, 56, 3689.
 Nising, C. F.; Brase, S. Chem. Soc. Rev. 2008, 37, 1218.
 Nising, C. F.; Brase, S. Chem. Soc. Rev. 2012, 41, 988.
 Heravi, M. M.; Hajiabbasi, P. Mol. Diversity 2014, 18, 411.
 Balasubramanian, K.; Selvaraj, S. Synthesis 1977, 767.
 Arct, J.; Jakubska, E.; Olszewska, G. Synthesis 1977, 314.
 Arct, J.; Jakubska, E.; Olszewska, G. Synth. Commun. 1978, 8, 143.
 Samarakoon, T. B.; Hur, M. Y.; Kurtz, R. D.; Hanson, P. R. Org. Lett. 2010, 12, 2182.
 Osyanin, V. A.; Nakushnov, V. Y.; Osipov, D. V.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2010, 46, 1027.
 Osyanin, V. A.; Osipov, D. V.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2010, 46, 377.
 Osyanin, V. A.; Nakushnov, V. Y.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2011, 47, 755.
 Osyanin, V. A.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2009, 45, 833.
 Sidorina, N. E.; Osyanin, V. A. Chem. Heterocycl. Compd. 2005, 41, 1201.
 Wang, P.; Song, Y.; Zhang, L.; He, H.; Zhou, X. Curr. Med. Chem. 2005, 12, 2893.
 Freccero, M. Mini-Rev. Org. Chem. 2004, 1, 403.
 Zhen, M. M.; Zhang, D. F.; Zhang, Z. Y.; Peng, Y. Q. ACS Comb. Sci. 2016, 18, 697.
 Erb, W.; Albini, M.; Rouden, J.; Blanchet, J. J. Org. Chem. 2014, 79, 10568.
 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.
 Yi Xiangyan, Zhang Zhipeng, Huang He, Baell Jonathan B., Yu Yang, Huang Fei. Microwave-Assisted Synthesis of α-Diazoesters[J]. Chin. J. Org. Chem., 2019, 39(2): 544-549.

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