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






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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) orcid , Abdel-Zaher Abdelaziz Elassar (2,*) orcid , Kamal Mohamed Dawood (3) orcid

(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)°, = 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).


Keywords


Bipyrazoles; C-C coupling; Heterocycles; Pd-complexes; X-ray single crystal; Bis-hydrazonoyl chlorides

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DOI: 10.5155/eurjchem.10.4.367-375.1915

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Funding information


This research work is funded by Kuwait University, research project grant SC-13/15.

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


Al-Fulaij, O.; Elassar, A.; Dawood, K. Eur. J. Chem. 2019, 10(4), 367-375. doi:10.5155/eurjchem.10.4.367-375.1915
Al-Fulaij, O.; Elassar, A.; Dawood, K. 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. Eur. J. Chem. 2019, 10(4), 367-375. doi:10.5155/eurjchem.10.4.367-375.1915
Al-Fulaij, O., Elassar, A., & Dawood, K. (2019). 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. European Journal of Chemistry, 10(4), 367-375. doi:10.5155/eurjchem.10.4.367-375.1915
Al-Fulaij, Othman, Abdel-Zaher Abdelaziz Elassar, & Kamal Mohamed Dawood. "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." European Journal of Chemistry [Online], 10.4 (2019): 367-375. Web. 22 Jan. 2020
Al-Fulaij, Othman, Elassar, Abdel-Zaher, AND Dawood, Kamal. "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" European Journal of Chemistry [Online], Volume 10 Number 4 (31 December 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.4.367-375.1915

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