Citation: Hong Gao, Jing Sun, Chao-Guo Yan. Synthesis of new type of Betti bases via three-component reaction of β-naphthol, cyclic amines and isatins[J]. Chinese Chemical Letters, ;2015, 26(3): 353-356. doi: 10.1016/j.cclet.2014.11.009
-
This work provided the first example of incorporating the oxindole moiety into the Betti bases. The new type of Betti bases were conveniently synthesized in good yields from the three-component reaction of β-naphthol, isatins and cyclic amines, such as piperidine ormorpholine, in methylene dichloride without any other catalyst.
-
Keywords:
- Betti base,
- Indolin-2-one,
- Piperidine,
- Morpholine,
- Three-component reaction
-
-
[1]
[1] M. Betti, β-naphthol phenylaminomethane, Org. Synth. Coll. 1 (1941) 381-384.
-
[2]
[2] C. Cardellicchio, M.A. Capozzi, A. Faso, The Betti base: the awakening of a sleeping beauty, Tetrahedron: Asymmetry 21 (2010) 507-517.
-
[3]
[3] B.P. Mathew, A. Kumar, S. Sharma, P.K. Shukla, M. Nath, An eco-friendly synthesis and antimicrobial activities of dihydro-2H-benzo-and naphtho-1,3-oxazine derivatives, Eur. J. Med. Chem. 45 (2010) 1502-1507.
-
[4]
[4] M. Salamone, R. Amorati, S. Menichetti, C. Viglianisi, M. Bietti, Structural and medium effects on the reactions of the cumyloxyl radical with intramolecular hydrogen bonded phenols. The interplay between hydrogen-bonding and acid-base interactions on the hydrogen atom transfer reactivity and selectivity, J. Org. Chem. 79 (2014) 6196-6205.
-
[5]
[5] P.F. Kaiser, J.M. White, C.A. Hutton, Enantioselective preparation of a stable boronate complex stereogenic only at boron, J. Am. Chem. Soc. 130 (2008) 16450-16451; G. Cheng, X. Wang, R. Zhu, et al., Total synthesis of (-)-cocaine and (-)-ferruginine, J. Org. Chem. 76 (2011) 2694-2700.
-
[6]
[6] X. Wang, Y. Dong, J. Sun, et al., Nonracemic Betti base as a new chiral auxiliary: application to total syntheses of enantiopure (2S,6R)-dihydropinidine and (2S,6R)-isosolenopsins, J. Org. Chem. 70 (2005) 1897-1900.
-
[7]
[7] H. Wei, L. Yin, H. Luo, X. Li, A.S.C. Chan, Structural influence of chiral tertiary aminonaphthol ligands on the asymmetric phenyl transfer to aromatic aldehydes, Chirality 23 (2011) 222-227.
-
[8]
[8] C. Cimarelli, D. Fratoni, A. Mazzanti, G. Palmieri, Enantiopure a-imino glyoxylate: a versatile substrate for the spontaneous asymmetric synthesis of unnatural hydroxyaryl glycinates, Tetrahedron: Asymmetry 22 (2011) 591-596.
-
[9]
[9] J. Lu, X. Xu, C. Wang, et al., Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes, Tetrahedron Lett. 43 (2002) 8367-8369.
-
[10]
[10] I. Szatmári, F. Fülöp, Microwave-assisted one-pot synthesis of (aminoalkyl)-naphthols and (aminoalkyl)quinolinols by using ammonium carbamate or ammonium hydrogen carbonate as solid ammonia source, Synthesis (2009) 775-778.
-
[11]
[11] I. Szatmári, F. Fülöp, Syntheses and transformations of 1-(a-aminobenzyl)-2-naphthol derivatives, Curr. Org. Synth. 1 (2004) 155-165.
-
[12]
[12] R. Csutortoki, I. Szatmári, F. Fülöp, Syntheses of amido-, carbamido-and carbamatoalkylnaphthols, Curr. Org. Synth. 10 (2013) 564-583.
-
[13]
[13] I. Szatmári, F. Fülöp, Syntheses, transformations and applications of aminonaphthol derivatives prepared via modified Mannich reactions, Tetrahedron 69 (2013) 1255.
-
[14]
[14] S.D. Dindulkar, V.G. Puranik, Y.T. Jeong, Supported copper triflate as an efficient catalytic system for the synthesis of highly functionalized 2-naphthol Mannich bases under solvent free condition, Tetrahedron Lett. 53 (2012) 4376-4380.
-
[15]
[15] A. Kumar, A. Saxena, M. Dewan, A. De, S. Mozumdar, Recyclable nanoparticulate copper mediated synthesis of naphthoxazinones in PEG-400: a green approach, Tetrahedron Lett. 52 (2011) 4835-4839.
-
[16]
[16] B. Karmakar, J. Banerji, A competent pot and atom-efficient synthesis of Betti bases over nanocrystalline MgO involving a modified Mannich type reaction, Tetrahedron Lett. 52 (2011) 4957-4960.
-
[17]
[17] A. Kumar, M.K. Gupta, M. Kumar, Non-ionic surfactant catalyzed synthesis of Betti base in water, Tetrahedron Lett. 51 (2010) 1582-1584.
-
[18]
[18] M. Shafiee, A.R. Khosropour, I. Mohammadpoor-Baltork, et al., An efficient, expeditious, and diastereoselective one-pot pseudo-five-component reaction for the synthesis of new bis-Betti bases under catalyst-free conditions, Tetrahedron Lett. 53 (2012) 3086-3090.
-
[19]
[19] M. Kidwai, R. Chauhan, Catalyst-free synthesis of Betti bases in a Mannich-type reaction, Asian J. Org. Chem. 2 (2013) 395-398.
-
[20]
[20] J. Sun, Y. Sun, H. Gong, Y.J. Xie, C.G. Yan, Facile synthesis of dispirooxindole-fused heterocycles via domino 1,4-dipolar addition and Diels-Alder reaction of in situ generated Huisgen 1,4-dipoles, Org. Lett. 14 (2012) 5172-5175.
-
[21]
[21] J. Sun, Y. Sun, H. Gao, C.G. Yan, Synthesis of spiro[indoline-3,20-quinoline] derivatives through a four-component reaction, Eur. J. Org. Chem. (2012) 1976-1983.
-
[22]
[22] H. Gong, J. Sun, C.G. Yan, Synthesis of triphenylphosphanylidene spiro[cyclopent[2]ene-1,30-indolines] with three-component reaction of triphenylphosphine, dialkyl acetylenedicarboxylates and 3-phenacylideneoxindoles, Synthesis (2014) 489-495.
-
[1]
-
-
[1]
Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
-
[2]
Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
-
[3]
Huixin Chen , Chen Zhao , Hongjun Yue , Guiming Zhong , Xiang Han , Liang Yin , Ding Chen . Unraveling the reaction mechanism of high reversible capacity CuP2/C anode with native oxidation POx component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650
-
[4]
Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
-
[5]
Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M2L4 coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
-
[6]
Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
-
[7]
Linjie Ju , Zhongxi Huang , Qian Shen , Chan Fu , Shuanghe Li , Wenjie Duan , Chenfeng Xu , Weizhen An , Zhiqiang Zhai , Jifu Wei , Changmin Yu , Guoren Zhou . Glutathione depletion based Pt(Ⅳ) hybrid mesoporous organosilica delivery system to conquer cisplatin chemoresistance: A “one stone three birds” strategy. Chinese Chemical Letters, 2024, 35(10): 109450-. doi: 10.1016/j.cclet.2023.109450
-
[8]
Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
-
[9]
Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
-
[10]
Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
-
[11]
Kunyao Peng , Xianbin Wang , Xingbin Yan . Converting LiNO3 additive to single nitrogenous component Li2N2O2 SEI layer on Li metal anode in carbonate-based electrolyte. Chinese Chemical Letters, 2024, 35(9): 109274-. doi: 10.1016/j.cclet.2023.109274
-
[12]
Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
-
[13]
Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
-
[14]
Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
-
[15]
Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
-
[16]
Pengfei Li , Chulin Qu , Fan Wu , Hu Gao , Chengyan Zhao , Yue Zhao , Zhen Shen . Robust free-base and metalated corrole radicals with reduction-induced emission. Chinese Chemical Letters, 2025, 36(2): 110292-. doi: 10.1016/j.cclet.2024.110292
-
[17]
Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
-
[18]
Wenhao Chen , Muxuan Wu , Han Chen , Lue Mo , Yirong Zhu . Cu2Se@C thin film with three-dimensional braided structure as a cathode material for enhanced Cu2+ storage. Chinese Chemical Letters, 2024, 35(5): 108698-. doi: 10.1016/j.cclet.2023.108698
-
[19]
Lanfang Wang , Jiangnan Lv , Yujia Li , Yanqing Hao , Wenjiao Liu , Hui Zhang , Xiaohong Xu . One-step synthesis of nanowoven ball-like NiS-WS2 for high-efficiency hydrogen evolution. Chinese Chemical Letters, 2025, 36(1): 109597-. doi: 10.1016/j.cclet.2024.109597
-
[20]
Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO2 nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(631)
- HTML views(30)