Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
Synthesis and characterization of new 3,3`-bipyrazole-4,4`-dicarboxylic acid derivatives and some of their palladium(II) complexes as pre-catalyst for Suzuki coupling reaction in water
Othman Abduallah Al-Fulaij (1)
, Abdel-Zaher Abdelaziz Elassar (2,*) , Kamal Mohamed Dawood (3) (1) Chemistry Department, Faculty of Science, Kuwait University, Safat-13060, Kuwait
(2) Chemistry Department, Faculty of Science, Kuwait University, Safat-13060, Kuwait
(3) Chemistry Department, Faculty of Science, Kuwait University, Safat-13060, Kuwait
(*) Corresponding Author
Received: 07 Jul 2019 | Revised: 20 Sep 2019 | Accepted: 27 Sep 2019 | Published: 31 Dec 2019 | Issue Date: December 2019
Abstract
The 1,3-dipolar cycloaddition reaction of bis-hydrazonyl chlorides with methyl propiolate afforded dimethyl 1,1¢-aryl-3,3`-bipyrazole-4,4`-dicarboxylates (5a,b). Heating the later compound 5a with a mixture of HCl/AcOH gave 3,3`-bipyrazole-5,5`-dicarboxylic acid derivative 6. Treatment of the hydrazonoyl chloride (1a) and 3,3`-bipyrazole-5,5`-dicarboxylic acid (6) with palladium(II) chloride gave the corresponding Pd-complexes 7 and 8, respectively. The catalytic activity of the prepared Pd-complexes was examined in the Suzuki cross-coupling reaction of phenylboronic acid with activated and deactivated aryl(hetaryl) bromides. The catalyst system provides very good to excellent yields, 85-94%. The structures of the obtained products were established from their elemental analysis, spectral data, XPS, EDX, and single crystal X-ray crystallography. Crystal data for C10H7N2O2 (6): triclinic, space group P-1 (no. 2), a = 3.9956(10) Å, b = 9.8917(18) Å, c = 10.810(3) Å, α = 94.167(15)°, β = 94.979(19)°, γ = 98.953(15)°, V = 418.83(16) Å3, Z = 2, T = 296.(2) K, μ(Cu Kα) = 0.887 mm-1, Dcalc = 1.484 g/cm3, 5469 reflections measured (11.72° ≤ 2Θ ≤ 133.24°), 1420 unique (Rint = 0.0633, Rsigma = 7.24%) which were used in all calculations. The final R1 was 0.1055 (>2sigma(I)) and wR2 was 0.3620 (all data).
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization between July 1, 2022 and August 15, 2022 (Voucher code: SINGLE2022).
2. Young writers will not be charged for the article processing fee between July 1, 2022 and August 15, 2022 (Voucher code: YOUNG2022).
3. The article processing fee will not be charged from the articles containing a part of the PhD thesis between July 1, 2022 and August 15, 2022 (Voucher code: PhD2022).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF
DOI: 10.5155/eurjchem.10.4.367-375.1915
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 848 times |
PDF Article downloaded 254 times
Funding information
This research work is funded by Kuwait University, research project grant SC-13/15.
Citations
[1]. Mohammad Suhail, Sofi Danish Mukhtar, Imran Ali, Ariba Ansari, Saiyam Arora
Theoretical DFT study of Cannizzaro reaction mechanism: A mini perspective
European Journal of Chemistry 11(2), 139, 2020
DOI: 10.5155/eurjchem.11.2.139-144.1975
[2]. Kamal M. Dawood, Ashraf A. Abbas
Synthetic Routes to Bioactive Bipyrazole Derivatives
ChemistrySelect 6(3), 279, 2021
DOI: 10.1002/slct.202003436
References
[1]. Ballhausen, C. J. Introduction to Ligand Field Theory, McGraw Hill, New York, 1962.
[2]. Atwood, J. D.; Wovkulich, M. J.; Sonnenberger, D. C. Acc. Chem. Res. 1983, 16, 350-355.
https://doi.org/10.1021/ar00093a006
[3]. Cotton, F. A.; Lin, C.; Murillo, C. A. Acc. Chem. Res. 2001, 34, 759-771.
https://doi.org/10.1021/ar010062+
[4]. Chifotides, H.; Dunbar, K. R. Acc. Chem. Res. 2005, 38, 146-156.
https://doi.org/10.1021/ar0302078
[5]. Muhammad, S.; Hussain, S.; Chen, X.; Al-Sehemi, A. G.; Li, Z. J.; Lai, C. -H.; Iqbal, J. Inorg. Chim. Acta 2019, 494, 160-167.
https://doi.org/10.1016/j.ica.2019.05.023
[6]. Fornies, J.; Martin, A.; Sicilia, V.; Martin, L. F. Chem. Eur. J. 2003, 9, 3427-3435.
https://doi.org/10.1002/chem.200204648
[7]. DeAngelis, A. J.; Peter, G. G.; Ruishan C.; Thomas J. C. J. Org. Chem. 2015, 80, 6794-6813.
https://doi.org/10.1021/acs.joc.5b01005
[8]. Ocansey, E.; Darkwa, J.; Makhubela, B. C. E. RSC Adv. 2018, 8, 13826-13834
https://doi.org/10.1039/C8RA01430B
[9]. Li, K.; Mohlala, M. S.; Segapelo, T. V.; Shumbula, P. M.; Guzei, I. A.; Darkwa, J. Polyhedron 2008, 27, 1017-1023.
https://doi.org/10.1016/j.poly.2007.11.033
[10]. Thakor, K. P.; Lunagariya1, M. V.; Bhatt, B. S.; Patel, M. N. Monatsh. Chem. 2019, 150, 233-245.
https://doi.org/10.1007/s00706-018-2316-6
[11]. Abdel-Wahab, B. F.; Dawood, K. M. Arkivoc 2012, 1, 491-545.
[12]. Rostom, S. A. F. Bioorg. Med. Chem. 2010, 18, 2767-2776.
https://doi.org/10.1016/j.bmc.2010.02.006
[13]. Bruno, O.; Ramise, A.; Bondavalli, F.; Schenone, P.; D'Amico, M.; Filippelli, A.; Filippelli, W.; Rossi, F. Il Farmaco 1993, 48, 949-966.
[14]. Abdel‐Aziz, S. A. G; Ali, T. E.; El‐Mahdy, K. M.; Somaia Mohamed Abdel‐Karim, S. Eur. J. Chem. 2011, 2, 25‐35.
https://doi.org/10.5155/eurjchem.2.1.25-35.208
[15]. Bouabdallah, I.; M'ebarek, A. L.; Zyad, A.; Ramdani, A.; Zidane, I.; Melhaoui, A. Nat. Prod. Res. 2007, 21, 298-302.
https://doi.org/10.1080/14786410701192801
[16]. Igarashi, T.; Sakurai, K.; Oi, T.; Obara, H.; Ohya, H.; Kamada, H. Free Radical Biol. Med. 1999, 26, 1339-1345.
https://doi.org/10.1016/S0891-5849(98)00291-3
[17]. Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347-1365.
https://doi.org/10.1021/jm960803q
[18]. Deng, X.; Mani, N. S. Org. Lett. 2008, 10, 1307-1310.
https://doi.org/10.1021/ol800200j
[19]. Padwa, A.; Pearson, W. H. Synthetic Applications of 1, 3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Wiley-Interscience; 1st edition, 2002.
https://doi.org/10.1002/0471221902
[20]. Padwa, A. Intramolecular 1, 3-Dipolar Cycloaddition. In Trost, B. M., Fleming, I. , Eds.; Comprehensive Organic Chemistry; Pergamon: Oxford, 1991, Vol. 4, pp. 1069.
https://doi.org/10.1016/B978-0-08-052349-1.00116-5
[21]. Behbehani, H.; Dawood, K. M.; Ibrahim, H. M.; Mostafa, N. S. Arab. J. Chem. 2018, 11, 1053-1060.
https://doi.org/10.1016/j.arabjc.2017.05.016
[22]. Behbehani, H.; Ibrahim, H. M.; Dawood, K. M. RSC Adv. 2015, 5, 25642-25649.
https://doi.org/10.1039/C5RA02972D
[23]. Dawood, K. M. Tetrahedron 2005, 61, 5229-5233.
https://doi.org/10.1016/j.tet.2005.03.083
[24]. Dawood, K. M.; Elwan, N. M. J. Chem. Res. 2004, 4, 264-266.
https://doi.org/10.3184/0308234041209121
[25]. Sheldrick, G. M. Acta. Cryst. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930
[26]. Dawood, K. M., MSc. Thesis, Synthesis and reactivity of some nitrogen and phosphorus dipoles, Cairo University, 1992.
[27]. Molander, G. A.; Petrillo, D. E.; Landzberg, N. R.; Rohanna, J. C.; Biolatto, B. Synlett. 2005, 11, 1763-1766.
https://doi.org/10.1055/s-2005-871544
[28]. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
https://doi.org/10.1021/ja992130h
[29]. Li, X.; Yan, X. Y.; Chang, H. H.; Wang, L. C.; Zhang, Y.; Chen, W. W.; Li, Y. W.; Wei, W. L. Org. Biomol. Chem. 2012, 10, 495- 497.
https://doi.org/10.1039/C1OB06752D
[30]. Lalitha, S.; Manoharan, P. T. J. Electron Spectrosc. Related Phenom. 1989, 49, 61-75.
https://doi.org/10.1016/0368-2048(89)80037-4
[31]. Liu, H.; Xue, X.; Li, T.; Wang, J.; Xu, W.; Liu, M.; Chen, P.; Wu, Y. RSC Adv. 2016, 6, 84815-84824.
https://doi.org/10.1039/C6RA14864F
[32]. Buscemi, G.; Basato, M.; Biffis, A.; Gennaro, A.; Isse, A. A. J. Organometal. Chem. 2010, 695, 2359-2365.
https://doi.org/10.1016/j.jorganchem.2010.06.019
[33]. Gustavo, D. S.; Rodrigues, M. A.; Silva, P. P.; Pereira-Maia, E. C.; Botelho, F. V.; Campos, T. A.; Franca, E. F.; Almeida, K. J.; Guerra, W. Croat. Chem. Acta 2013, 86, 201-206.
https://doi.org/10.5562/cca2151
[34]. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008, 64, 3047-3101.
https://doi.org/10.1016/j.tet.2007.12.036
[35]. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
https://doi.org/10.1021/cr00039a007
[36]. Dawood, K. M.; Fayed, M. S.; Elkhalea, M. M. Arkivoc 2009, 13, 324-341.
[37]. Elassar, A. Z. A. J. Heterocyl. Chem. 2011, 48, 272-278
https://doi.org/10.1002/jhet.545
Supporting information
The Supplementary Material for this article can be found online at: Supplementary files
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.10.4.367-375.1915
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2019, 10(4), 367-375 | doi: https://doi.org/10.5155/eurjchem.10.4.367-375.1915 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c) 2019 Authors
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).
© Copyright 2010 - 2022 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2022 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.