Citation: Behnaz Afzalian, Joel T. Mague, Maryam Mohamadi, S. Yousef Ebrahimipour, Behjat Pour amiri, Esmat Tavakolinejad Kermani. Ni(II), Co(II), and Cu(II) complexes incorporating 2-pyrazinecarboxylic acid: Synthesis, characterization, electrochemical evaluation, and catalytic activity for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones[J]. Chinese Journal of Catalysis, ;2015, 36(7): 1101-1108. doi: 10.1016/S1872-2067(14)60318-1 shu

Ni(II), Co(II), and Cu(II) complexes incorporating 2-pyrazinecarboxylic acid: Synthesis, characterization, electrochemical evaluation, and catalytic activity for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones

1.
a Department of Chemistry, Payam Noor University (PNU), 19395-4697 Tehran, Iran;

Corresponding author: S. Yousef Ebrahimipour,
Received Date: 11 January 2015
Available Online: 10 February 2015

Three complexes containing 2-pyrazinecarboxylate (pzca^-), including [Ni(pzca)₂(H₂O)₂], [Co(pzca)₂(H₂O)₂], and [Cu(pzca)₂(H₂O)₂], have been synthesized and characterized using physicochemical and spectroscopic methods. Furthermore, the structure of each complex was determined by single-crystal X-ray diffraction. All three complexes have an octahedral geometry, where the metal ion chelated by two carboxylate oxygens, two nitrogen atoms belonging to pyrazinic acid molecules, and two oxygen atoms of two water molecules. The catalytic activities of these complexes were also investigated in the green synthesis of 2H-indazolo[2,1-b]phthalazine-triones by the reaction of hydrazine hydrate with an arylaldehyde, phthalic anhydride, and dimedone in acetic acid.
- 2-Pyrazinecarboxylate complexe,
- ON bidentate ligand,
- X-ray crystal structure,
- Cyclic voltammetry,
- 2H-indazolo[2,1-b]phthalazine-triones
1. [1]
  [1] Khabazzadeh H, Sheikhshoaie I, Saeid-Nia S. Transit Met Chem, 2010, 35: 125
2. [2]
  [2] Zhu J, Bienaymé H. Multicomponent Reactions. New York: John Wiley & Sons, 2006
3. [3]
  [3] Armstrong R W, Combs A P, Tempest P A, Brown S D, Keating T A. Acc Chem Res, 1996, 29: 123
4. [4]
  [4] Joule J A, Mills K. Heterocyclic Chemistry. 5th Ed. New York: John Wiley & Sons, 1999
5. [5]
  [5] Khalil A M, Berghot M A, Gouda M A. Eur J Med Chem, 2009, 44: 4448
6. [6]
  [6] Grasso S, De Sarro G, De Sarro A, Micale N, Zappalà M, Puja G, Baraldi M, De Micheli C. J Med Chem, 2000, 43: 2851
7. [7]
  [7] Nomoto Y, Obase H, Takai H, Teranishi M, Nakamura J, Kubo K. Chem Pharm Bull, 1990, 38: 2179
8. [8]
  [8] Watanabe N, Kabasawa Y, Takase Y, Matsukura M, Miyazaki K, Ishihara H, Kodama K, Adachi H. J Med Chem, 1998, 41: 3367
9. [9]
  [9] Shaterian H R, Ghashang M, Feyzi M. Appl Catal A, 2008, 345: 128
10. [10]
  [10] Tavakoli H R, Moosavi S M, Bazgir A. J Korean Chem Soc, 2013, 57: 472
11. [11]
  [11] Sabitha G, Srinivas C, Raghavendar A, Yadav J S. Helv Chim Acta, 2010, 93: 1375
12. [12]
  [12] Khurana J M, Magoo D. Tetrahedron Lett, 2009, 50: 7300
13. [13]
  [13] Mazaahir K, Ritika C, Anwar J. Chin Sci Bull, 2012, 57: 2273
14. [14]
  [14] Mosaddegh E, Hassankhani A. Tetrahedron Lett, 2011, 52: 488
15. [15]
  [15] Ebrahimipour S Y, Sheikhshoaie I, Crochet A, Khaleghi M, Fromm K M. J Mol Struct, 2014, 1072: 267.
16. [16]
  [16] Ebrahimipour S Y, Mohamadi M, Castro J, Mollania N, Amiri Rudbari H, Sacca A. J Coord Chem, 2015, 68: 632
17. [17]
  [17] Hoseini Monfared H, Kheiabadi S, Asghari Lalami N, Mayer P. Polyhedron, 2011, 30: 1375
18. [18]
  [18] Ebrahimipour S Y, Ranjbar Z R, Kermani E T, Amiri B P, Amiri Rudbari H, Sacca A, Hoseinzade F. Transit Met Chem, 2015, 40: 39
19. [19]
  [19] Ebrahimipour S Y, Khabazadeh H, Castro J, Sheikhshoaie I, Crochet A, Fromm K M. Inorg Chim Acta, 2015, 427: 52
20. [20]
  [20] APEX2, SADABS, SHELXT and SHELXTL. Bruker, Madison, WI, USA, 2013
21. [21]
  [21] Sheldrick G. SHELXL-2013. University of Göttingen Göttingen, Germany, 2013
22. [22]
  [22] El-Medani S M, Ali O A M, Mohamed H A, Ramadan R M. J Coord Chem, 2005, 58: 1429
23. [23]
  [23] O'Connor C J, Sinn E. Inorg Chem, 1981, 20: 545
24. [24]
  [24] Ptasiewicz-Bąk H, Leciejewicz J, Zachara J. J Coord Chem, 1995, 36: 317
25. [25]
  [25] Zhang F, Hao L, Zhang L J, Zhang X G. Int J Electrochem Sci, 2011, 6: 2943
26. [26]
  [26] Ebrahimipour S Y, Abaszadeh M, Castro J, Seifi M. Polyhedron, 2014, 79: 138
27. [27]
  [27] Ebrahimipour S Y, Sheikhshoaie I, Mohamadi M, Suarez S, Baggio R, Khaleghi M, Torkzadeh-Mahani M, Mostafavi A. Spectrochim Acta A, 2015, 142: 410
28. [28]
  [28] Ebrahimipour S Y, Mague J T, Akbari A, Takjoo R. J Mol Struct, 2012, 1028: 148
29. [29]
  [29] Takjoo R, Mague J T, Akbari A, Ebrahimipour S Y. J Coord Chem, 2013, 66: 2852
30. [30]
  [30] Sayyafi M, Seyyedhamzeh M, Khavasi H R, Bazgir A. Tetrahedron, 2008, 64: 2375
31. [31]
  [31] Shaterian H R, Hosseinian A, Ghashang M. Arkivoc, 2009, (11): 59
32. [32]
  [32] Shukla G, Verma R K, Verma G K, Singh M S. Tetrahedron Lett, 2011, 52: 7195
33. [33]
  [33] Rostamnia S, Doustkhah E. Tetrahedron Lett, 2014, 55: 2508
34. [34]
  [34] Hasaninejed A, Kazerooni M R, Zare A. Catal Today, 2012, 196: 148
35. [35]
  [35] Shekouhy M, Hasaninejad A. Ultrason Sonochem, 2012, 19: 307
36. [36]
  [36] Shaterian H R, Aghakhanizadeh M. C R Chimie, 2012, 15: 1060
37. [37]
  [37] Kiasat A R, Noorizadeh S, Ghahremani M, Saghanejad S J. J Mol Struct, 2013, 1036: 216
1. [1]
  Cen Zhou , Biqiong Hong , Yiting Chen . Application of Electrochemical Techniques in Supramolecular Chemistry. University Chemistry, 2025, 40(3): 308-317. doi: 10.12461/PKU.DXHX202406086
2. [2]
  Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
3. [3]
  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
4. [4]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
5. [5]
  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
6. [6]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
7. [7]
  Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
8. [8]
  Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
9. [9]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
10. [10]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
11. [11]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
12. [12]
  Haiming Wu , Gaya N. Andrew , Rajini Anumula , Zhixun Luo . Corrigendum to 'How ligand coordination and superatomic-states accommodate the structure and property of a metal cluster: Cu₄ (dppy)₄ Cl₂ vs. Cu₂₁ (dppy)₁₀ with altered photoluminescence' [Chin. Chem. Lett. 35 (2024) 108340]. Chinese Chemical Letters, 2024, 35(12): 109912-. doi: 10.1016/j.cclet.2024.109912
13. [13]
  Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
14. [14]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
15. [15]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
16. [16]
  Jijoe Samuel Prabagar , Kumbam Lingeshwar Reddy , Dong-Kwon Lim . Visible-light responsive gold nanoparticle and nano-sized Bi2O3-x sheet heterozygote structure for efficient photocatalytic conversion of N2 to NH3. Chinese Journal of Structural Chemistry, 2025, 44(4): 100564-100564. doi: 10.1016/j.cjsc.2025.100564
17. [17]
  Ruowen Liang , Chao Zhang , Guiyang Yan . Enhancing CO2 cycloaddition through ligand functionalization: A case study of UiO-66 metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(2): 100211-100211. doi: 10.1016/j.cjsc.2023.100211
18. [18]
  Huirong Chen , Yingzhi He , Yan Han , Jianbo Hu , Jiantang Li , Yunjia Jiang , Basem Keshta , Lingyao Wang , Yuanbin Zhang . A new SIFSIX anion pillared cage MOF with crs topological structure for efficient C2H2/CO2 separation. Chinese Journal of Structural Chemistry, 2025, 44(2): 100508-100508. doi: 10.1016/j.cjsc.2024.100508
19. [19]
  Luyan Shi , Ke Zhu , Yuting Yang , Qinrui Liang , Qimin Peng , Shuqing Zhou , Tayirjan Taylor Isimjan , Xiulin Yang . Phytic acid-derivative Co₂B-CoPO_x coralloidal structure with delicate boron vacancy for enhanced hydrogen generation from sodium borohydride. Chinese Chemical Letters, 2024, 35(4): 109222-. doi: 10.1016/j.cclet.2023.109222
20. [20]
  Yaqi Deng , Jian Xue , Xiang Wu , Shunying Liu . Highly regioselective electrochemical oxidative 2,1-azolization of alkenes with azoles and nucleophiles. Chinese Chemical Letters, 2025, 36(9): 110822-. doi: 10.1016/j.cclet.2025.110822

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(373)
HTML views(30)

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