Citation: Wang Fang-Fang, Deng Ya-Xin, Chao Huang, Zhang Qi-Long, Zhu Bi-Xue. One-pot synthesis of [1+1] and 62-membered [2+2] Schiff base macrocycles[J]. Chinese Chemical Letters, ;2016, 27(9): 1551-1553. doi: 10.1016/j.cclet.2016.02.031 shu

One-pot synthesis of [1+1] and 62-membered [2+2] Schiff base macrocycles

a.
Key Laboratory of Macrocyclic and Supramolecular Chemistry, Guizhou University, Guiyang 550025, China
b.
Department of Chemistry, Guizhou Medical College, Guiyang 550004, China

Corresponding author: Zhang Qi-Long, gzuqlzhang@126.com Zhu Bi-Xue, sci.bxzhu@gzu.edu.cn
Received Date: 9 January 2016
Revised Date: 3 February 2016
Accepted Date: 29 February 2016
Available Online: 24 September 2016

Figures(2)

New [1+1] and 62-membered [2+2] Schiff base macrocycles containing a 2, 6-diamidopyridine subunit have been synthesized by condensation reaction of the precursors pyridine-2, 6-dicarboxamide and 1, 10-bis(20-formylphenyloxy)decane in the presence of phosphoric acid via a one-pot process. The cyclocondensed products were effectively isolated by gel column chromatography and characterized by ¹H NMR, FTIR, mass spectrometry and X-ray analysis. The two macrocycles have a twisted structure, and not an open ‘circular’ conformation in the solid state.
- Macrocycles,
- Schiff base,
- One-pot synthesis,
- Crystal structure
1. [1]
  R.M. Corral, H. Höpfl, L.M. Lara, et al., Synthesis, structural characterization and metal inclusion properties of 18-20-and 22-membered oxaazacyclophanes and oxaazacalix[4] arene analogues:macrocyclic amine and Schiff base receptors with variable N_xO_y donor sets, Eur. J. Org. Chem. (2011) 2148-2162.
2. [2]
  Rajakumara P., Rasheed A.M.A.. Synthesis, characterization and ion transportation studies of some novel cyclophane amides[J]. Tetrahedron, 2005,61:5351-5362. doi: 10.1016/j.tet.2005.03.064
3. [3]
  Paryzek W.R., Patroniak V., Lisowski J.. Metal complexes of polyaza and polyoxaaza Schiff base macrocycles[J]. J. Coord. Chem. Rev., 2005,249:2156-2175. doi: 10.1016/j.ccr.2005.02.021
4. [4]
  Chen S.S., Yan Q.F., Li T.. Arylene ethynylene macrocycles with intramolecular π-π stacking[J]. Org. Lett., 2010,12:4784-4787. doi: 10.1021/ol101914f
5. [5]
  Wu Z.H., Hu T., He L.. One-pot formation of aromatic tetraurea macrocycles[J]. Org. Lett., 2012,14:2504-2507. doi: 10.1021/ol300684j
6. [6]
  Borisova N.E., Reshetova M.D., Ustynyuk Y.A.. Metal-free methods in the synthesis of macrocyclic Schiff bases[J]. Chem. Rev., 2007,107:46-79. doi: 10.1021/cr0683616
7. [7]
  Vigato P.A., Tamburini S.. The challenge of cyclic and acyclic schiff bases and related derivatives[J]. Coord. Chem. Rev., 2004,248:1717-2128. doi: 10.1016/j.cct.2003.09.003
8. [8]
  Kal S., Filatov A.S., Dinolfo P.H.. Structural, electrochemical, and spectroscopic investigation of acetate bridged dinuclear Tetrakis-Schiff base macrocycles of Mn and Zn[J]. Inorg. Chem., 2013,52:13963-13973. doi: 10.1021/ic401631e
9. [9]
  Zhang K., Jin C., Sun Y.-C.. Base-induced self-assembly for one-dimensional coordination polymers via chiral pendant-armed Schiff base mononuclear Pb(Ⅱ) macrocycles[J]. Inorg. Chem., 2014,53:7803-7805. doi: 10.1021/ic5008846
10. [10]
  Jiang J., Dong R.Y., MacLachlan M.J.. Lyotropic liquid crystallinity in mixedtautomer Schiff-base macrocycles[J]. Chem. Commun., 2015,51:16205-16208. doi: 10.1039/C5CC06253E
11. [11]
  Ou M., Zhu C., Zhang Q.-L.. Synthesis and characterization of macrocyclic compounds with a hydroxyl functional group[J]. Chin. Chem. Lett., 2013,24:869-872. doi: 10.1016/j.cclet.2013.06.014
12. [12]
  Yuan Z.-L., Zhang Q.-L., Liang X.. A new series of dinucleating macrocyclic ligands and their complexes of zinc(Ⅱ)[J]. Polyhedron, 2008,27:344-348. doi: 10.1016/j.poly.2007.09.012
13. [13]
  Zhang D.-W., Zhao X., Hou J.-L.. Aromatic amide foldamers:structures, properties, and functions[J]. Chem. Rev., 2012,112:5271-5316. doi: 10.1021/cr300116k
14. [14]
  Kang S.O., Day V.W., Bowman-James K.. Fluoride:solution-and solid-state structural binding probe[J]. J. Org. Chem., 2010,75:277-283. doi: 10.1021/jo901581w
15. [15]
  Katayev E.A., Pantos G.D., Reshetova M.D.. Anion-induced synthesis and combinatorial selection of polypyrrolic macrocycles[J]. Angew. Chem. Int. Ed., 2005,44:7386-7390. doi: 10.1002/(ISSN)1521-3773
16. [16]
  Katayev E.A., Sessler J.L., Khrustalev V.N.. Synthetic model of the phosphate binding protein:solid-state structure and solution-phase anion binding properties of a large oligopyrrolic macrocycle[J]. J. Org. Chem., 2007,72:7244-7252. doi: 10.1021/jo071106g
17. [17]
  Kang S.O., Day V.W., Bowman-James K.. The influence of amine functionalities on anion binding in polyamide-containing macrocycles[J]. Org. Lett., 2009,11:3654-3657. doi: 10.1021/ol9014249
18. [18]
  Liao J.-H., Chen C.-T., Fang J.-M.. A novel phosphate chemosensor utilizing anioninduced fluorescence change[J]. Org. Lett., 2002,4:561-564. doi: 10.1021/ol0171564
19. [19]
  Ema T., Tanida D., Sugita K.. Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity[J]. Org. Lett., 2008,10:2365-2368. doi: 10.1021/ol800940j
20. [20]
  Hu P., Guo S.-Y., Zhang Q.-L.. Synthesis, characterization of novel[1+1] Schiff base macrocyclic compounds[J]. Chin. J. Org. Chem., 2013,33:325-331. doi: 10.6023/cjoc201210010
21. [21]
  Cerrada P., Oriol L., Pinol M.. Alternative synthetic strategies for Schiff base derived liquid crystal polymers:a comparative study[J]. J. Polym. Sci. A:Poly Chem., 1996,34:2603-2611. doi: 10.1002/(ISSN)1099-0518
22. [22]
  Akine S., Kusama D., Takatsuki Y.. Synthesis of tetrafunctionalized pentiptycenequinones for construction of cyclic dimers with a cylindrical shape by boronate ester formation[J]. Tetrahedron Lett., 2015,56:4880-4884. doi: 10.1016/j.tetlet.2015.06.070
23. [23]
  Shimakoshi H., Kai T., Aritome I.. Syntheses of large-membered macrocycles having multiple hydrogen bonding moieties[J]. Tetrahedron Lett., 2002,43:8261-8264. doi: 10.1016/S0040-4039(02)02022-1
1. [1]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
2. [2]
  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
3. [3]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
4. [4]
  Muhammad Riaz , Rakesh Kumar Gupta , Di Sun , Mohammad Azam , Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427
5. [5]
  Tiantian Li , Ruochen Jin , Bin Wu , Dongming Lan , Yunjian Ma , Yonghua Wang . A novel insight of enhancing the hydrogen peroxide tolerance of unspecific peroxygenase from Daldinia caldariorum based on structure. Chinese Chemical Letters, 2024, 35(4): 108701-. doi: 10.1016/j.cclet.2023.108701
6. [6]
  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
7. [7]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
8. [8]
  Dan Luo , Jinya Tian , Jianqiao Zhou , Xiaodong Chi . Anthracene-bridged "Texas-sized" box for the simultaneous detection and uptake of tryptophan. Chinese Chemical Letters, 2024, 35(9): 109444-. doi: 10.1016/j.cclet.2023.109444
9. [9]
  Xinyi Cao , Yucheng Jin , Hailong Wang , Xu Ding , Xiaolin Liu , Baoqiu Yu , Xiaoning Zhan , Jianzhuang Jiang . A tetraaldehyde-derived porous organic cage and covalent organic frameworks: Syntheses, structures, and iodine vapor capture. Chinese Chemical Letters, 2024, 35(9): 109201-. doi: 10.1016/j.cclet.2023.109201
10. [10]
  Zhexin Chen , Yuqing Shi , Fang Zhong , Kai Zhang , Furong Zhang , Shenghong Xie , Zhongbin Cheng , Qian Zhou , Yi-You Huang , Hai-Bin Luo . Discovery of amentoflavone as a natural PDE4 inhibitor with anti-fibrotic effects. Chinese Chemical Letters, 2025, 36(4): 109956-. doi: 10.1016/j.cclet.2024.109956
11. [11]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
12. [12]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
13. [13]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
14. [14]
  Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
15. [15]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268
16. [16]
  Wen-Hui Mi , Teng-Yu Huang , Yu-Fei Ao , Xu-Dong Wang , Qi-Qiang Wang , De-Xian Wang . Ultracycles consisting of macrocycles. Chinese Chemical Letters, 2024, 35(5): 109077-. doi: 10.1016/j.cclet.2023.109077
17. [17]
  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
18. [18]
  Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994
19. [19]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
20. [20]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(691)
HTML views(8)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142