Scandium(Ⅲ)-Catalyzed Aza-Michael Addition of in Situ Generated ortho-Quinone Methides with Amines: An Efficient Access to Betti Base Derivatives
- Corresponding author: Zhang Shuo, e50687e@163.com Peng Dan, lonarpeng@aliyun.com
Citation:
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
Betti, M. Org. Synth. 1929, 9, 60
doi: 10.15227/orgsyn.009.0060
Waisser, K.; Gregor, K.; Kubicova, L.; Klimesova, V.; Kunes, J.; Machacek, M. Eur. J. Med. Chem. 2000, 35, 733.
doi: 10.1016/S0223-5234(00)00174-4
Bouaziz, Z.; Riondel, J.; Mey, A.; Berlion, M.; Villard, J.; Filliond, H. Eur. J. Med. Chem. 1991, 26, 469.
doi: 10.1016/0223-5234(91)90109-Z
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.
doi: 10.1021/jm00341a004
Benameur, L.; Bouaziz, Z.; Nebois, P.; Bartoli, M. H.; Boitard, M.; Chem. Pharm. Bull. 1996, 44, 605.
doi: 10.1248/cpb.44.605
Mathew, B. P.; Kumar, A.; Sharma, S.; Shukla, P. K.; Nath, M. Eur. J. Med. Chem. 2010, 45, 1502.
doi: 10.1016/j.ejmech.2009.12.058
Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron. Lett. 2002, 43, 8367.
doi: 10.1016/S0040-4039(02)01985-8
Feng, J.; Bohle, D. S.; Li, C. J. Tetrahedron:Asymmetry 2007, 18, 1043.
doi: 10.1016/j.tetasy.2007.05.005
Kidwai, M.; Chauhan, R. Asian J. Org. Chem. 2013, 2, 395.
doi: 10.1002/ajoc.v2.5
Safari, J.; Zarnegar, Z. J. Mol. Catal. A:Chem. 2013, 379, 269.
doi: 10.1016/j.molcata.2013.08.028
Hajjami, M.; Ghorbani, F.; Bakhti, F. Appl. Catal. A 2014, 470, 303.
doi: 10.1016/j.apcata.2013.11.002
Hajipour, A. R.; Ghayeb, Y.; Sheikhan, N.; Ruoho, A. E. Tetrahedron Lett. 2009, 50, 5649.
doi: 10.1016/j.tetlet.2009.07.116
Pathak, T. P.; Sigman, M. S. J. Org. Chem. 2011, 76, 9210.
doi: 10.1021/jo201789k
Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18, 9160.
doi: 10.1002/chem.v18.30
Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.
doi: 10.3390/molecules200711733
Wang, Z.; Sun, J. Synthesis 2015, 47, 3629.
doi: 10.1055/s-00000084
Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
doi: 10.1016/S0040-4020(02)00496-9
Kulikov, A.; Arumugam, S.; Popik, V. V. J. Org. Chem. 2008, 73, 7611.
doi: 10.1021/jo801302m
Mattson, A. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 4508
doi: 10.1021/ja068189n
Luan, Y.; Schaus, S. E. J. Am. Chem. Soc. 2012, 134, 19965.
doi: 10.1021/ja309076g
Shaikh, A. K.; Cobb, A. J. A.; Varounis, G. Org. Lett. 2012, 14, 584.
doi: 10.1021/ol203196n
Chen, M. W.; Gao, L. L.; Ye, Z. S.; Jiang, G. F.; Zhou, Y. G. Chem. Commun. 2013, 49, 1660.
doi: 10.1039/c3cc37800d
Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. A. Org. Lett. 2004, 6, 4049.
doi: 10.1021/ol048298b
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.
doi: 10.1021/ar500330x
Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.
doi: 10.3390/molecules200711733
Liang, M.; Zhang, S.; Jia, J.; Tung, C.-H.; Wang, J.; Xu, Z. Org. Lett. 2017, 19, 2526.
doi: 10.1021/acs.orglett.7b00804
Zhao, W.; Wang, Z.; Chu, B.; Sun, J. Angew. Chem., Int. Ed. 2015, 54, 1910.
doi: 10.1002/anie.201405252
Huang, Y.; Hayashi, T. J. Am. Chem. Soc. 2015, 137, 7556.
doi: 10.1021/jacs.5b03277
Wang, Z.; Ai, F.; Wang, Z.; Zhao, W.; Zhu, G.; Lin, Z.; Sun, J. J. Am. Chem. Soc. 2015, 137, 383.
doi: 10.1021/ja510980d
Wu, B.; Yu, Z.; Gao, X.; Lan, Y.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2017, 56, 4006.
doi: 10.1002/anie.201700437
Chen, P.; Wang, K. l; Guo, W.; Liu, X.; Liu, Y.; Li, C. Angew. Chem., Int. Ed. 2017, 56, 3689.
doi: 10.1002/anie.201700250
Nising, C. F.; Brase, S. Chem. Soc. Rev. 2008, 37, 1218.
doi: 10.1039/b718357g
Nising, C. F.; Brase, S. Chem. Soc. Rev. 2012, 41, 988.
doi: 10.1039/C1CS15167C
Heravi, M. M.; Hajiabbasi, P. Mol. Diversity 2014, 18, 411.
doi: 10.1007/s11030-013-9494-2
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.
doi: 10.1080/00397917808065600
Samarakoon, T. B.; Hur, M. Y.; Kurtz, R. D.; Hanson, P. R. Org. Lett. 2010, 12, 2182.
doi: 10.1021/ol100495w
Osyanin, V. A.; Nakushnov, V. Y.; Osipov, D. V.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2010, 46, 1027.
doi: 10.1007/s10593-010-0622-y
Osyanin, V. A.; Osipov, D. V.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2010, 46, 377.
doi: 10.1007/s10593-010-0522-1
Osyanin, V. A.; Nakushnov, V. Y.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2011, 47, 755.
doi: 10.1007/s10593-011-0830-0
Osyanin, V. A.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2009, 45, 833.
doi: 10.1007/s10593-009-0350-3
Sidorina, N. E.; Osyanin, V. A. Chem. Heterocycl. Compd. 2005, 41, 1201.
doi: 10.1007/s10593-005-0306-1
Sidorina, N. E.; Osyanin, V. A. Chem. Heterocycl. Compd. 2007, 43, 1065
doi: 10.1007/s10593-007-0166-y
Wang, P.; Song, Y.; Zhang, L.; He, H.; Zhou, X. Curr. Med. Chem. 2005, 12, 2893.
doi: 10.2174/092986705774454724
Freccero, M. Mini-Rev. Org. Chem. 2004, 1, 403.
doi: 10.2174/1570193043403091
Zhang, S.; Peng, D.; Zhao, N.; Yu, Y.; Wang, F.; Liu, H.; Yi, G. Chin. J. Org. Chem. 2019, 39, 555(in Chinese).
Zhen, M. M.; Zhang, D. F.; Zhang, Z. Y.; Peng, Y. Q. ACS Comb. Sci. 2016, 18, 697.
doi: 10.1021/acscombsci.6b00090
Erb, W.; Albini, M.; Rouden, J.; Blanchet, J. J. Org. Chem. 2014, 79, 10568.
doi: 10.1021/jo501665e
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.
doi: 10.1021/jo9903609
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
Yifan Liu , Haonan Peng . AI-Assisted New Era in Chemistry: A Review of the Application and Development of Artificial Intelligence in Chemistry. University Chemistry, 2025, 40(7): 189-199. doi: 10.12461/PKU.DXHX202405182
Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO2制C2+产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
Yunchao Li , Shanying Chen , Ke Qi , Kangning Huo , Shuxin Li , Jingyi Li , Ying Wei , Louzhen Fan . A New Colloid Electrophoresis Experiment Incorporating Characteristics of Inquiry Learning and Ideological and Political Education. University Chemistry, 2024, 39(2): 47-51. doi: 10.3866/PKU.DXHX202308063
Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C60-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
Yiming Lu , Xiang Xie , Xiaoqing Qiu , Yang Liu , Xinyuan Cheng . The New Year’s Eve of the Aviation Brake Material Family. University Chemistry, 2024, 39(9): 203-207. doi: 10.12461/PKU.DXHX202403061
Ruiyuan Xu , Yuxin Wang , Yuru Zhang , Wanmei Li . Who Destroyed Snowflake Castle. University Chemistry, 2024, 39(9): 224-228. doi: 10.12461/PKU.DXHX202311056
Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
Xudong Liu , Huili Fan , Junping Xiao , Min Yang , Yan Li . Teaching Approaches to the AE + AN Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016