European Journal of Chemistry

Synthesis and DFT study of novel pyrazole, thiophene, 1,3-thiazole and 1,3,4-thiadiazole derivatives

Crossmark


Main Article Content

Asmaa Mahmoud Fahim
Ahmad Mahmoud Farag
Mohamed Rabie Shaaban
Eman Ali Ragab

Abstract

Regioselective facile synthesis of innovative heterocycles from the reaction of 2-cyano-N-cyclohexylacetamide (3) with hydrazonoyl chloride (4) in basic condition afforded amino pyrazole derivative 6. The behavior of acetamide 3 with phenylisothiocyanate in DMF/KOH surveyed by addition of the α-halo ketones to yeild the corresponding thiophene derivative 13a, 13b, 16, 18 and 1,3-thiazoles 21. Reaction of intermediate potassium salt 9 with hydrazonoyl chloride 22a-e furnished the corresponding 1,2,4-thiadiazoles 24a-e. Density functional theory (DFT) calculations at the B3LYP and HF techniques combined with 6-31G(d) basis set to investigate the equilibrium geometry of the innovative compound pyrazoles 6 and the stability affording of HOMO/LUMO molecular orbitals.


icon graph This Abstract was viewed 2603 times | icon graph Article PDF downloaded 911 times

How to Cite
(1)
Fahim, A. M.; Farag, A. M.; Shaaban, M. R.; Ragab, E. A. Synthesis and DFT Study of Novel Pyrazole, Thiophene, 1,3-Thiazole and 1,3,4-Thiadiazole Derivatives. Eur. J. Chem. 2018, 9, 30-38.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Ammar, Y. A.; Samir, Y. A.; Ghorab, M. M.; Mansour, S. A. Tetrahedron Lett. 2016, 57, 275-277.
https://doi.org/10.1016/j.tetlet.2015.11.098

[2]. Ammar, Y. A.; Ali, M. M.; Mohamed, Y. A.; Thabet, H. K.; El-Gaby, M. S. A. Heterocycl. Commun. 2013, 19, 195-200.
https://doi.org/10.1515/hc-2013-0032

[3]. Farag, A. A.; Abd-Alrahman, S. N.; Ahmed, G. F.; Ammar, R. M.; Ammar, Y. A.; Abbas, S. Y. Arch. Pharm. Life Sci. 2012, 345, 703-712.
https://doi.org/10.1002/ardp.201200014

[4]. Ammar, Y. A.; Aly, M. M.; Al-Sehemi, A. G.; Salem, M. A.; El-Gaby, M. S. A. J. Chin. Chem. Soc. 2009, 183, 1064-1068.
https://doi.org/10.1002/jccs.200900154

[5]. Dawood, K. M.; Abdel-Gawad, H.; Ragab, E. A. Bioorg. Med. Chem. 2006, 14, 3672-3680.
https://doi.org/10.1016/j.bmc.2006.01.033

[6]. Dawood, K. M.; Ragab, E. A.; Farag, A. M. Phosphorus, Sulfur, Silicon 2010, 185, 1796-1802.
https://doi.org/10.1080/10426500903299919

[7]. Fadda, A. A.; Bondock, S.; Rabie, R.; Etman, H. A. Turk. J. Chem. 2008, 32, 259-286.

[8]. Abdul, R.; Khalil, A. N.; Nasim, F. H.; Yand, A.; Qureshi, A. M. Eur. J. Chem. 2015, 6(2), 163‐168.
https://doi.org/10.5155/eurjchem.6.2.163-168.1224

[9]. Rauf, A.; Liaqat, S.; Qureshi, A. M.; Yaqub, M.; Rehman, A. U.; Hassan, M. U.; Chohan, Z. H.; Nasim, F. U. H.; Hadda, T. B. J. Med. Chem. Res. 2012, 21, 60‐74.
https://doi.org/10.1007/s00044-010-9491-2

[10]. El-Kashef, H. S.; El-Emary, T. I.; Gasquet, M.; Timon-David, P.; Maldonado, J.; Vanelle, P. Pharmazie 2000, 55, 572-576.

[11]. Ammar, Y. A.; El-Sharief, A. M. S.; Al-Sehemi, A. G.; Mohamed, Y. A.; El-Hag Ali, G. A. M.; Senussi, M. A.; El-Gaby, M. S. A. Phosphorus, Sulfur Silicon 2005, 180(11), 2503-2506.
https://doi.org/10.1080/104265090929887

[12]. Dyachenko, V. D.; Tkachiov, R. P.; Bityukova, O. S. Russ. J. Org. Chem. 2008, 44, 1565-1570.
https://doi.org/10.1134/S1070428008110018

[13]. El-Ghayati, L.; Ramli, Y.; El-Mokhtar, E.; Mohamed, L. T.; Joel, T. M. IUCrData 2016, 1, x160947.
https://doi.org/10.1107/S2414314616009470

[14]. Clarissa, P. F.; Elisandra, S.; Patrick, T. C.; Dayse, N. M.; Marcos, A. P. M. J. Mol. Struc. 2009, 933, 142-147.
https://doi.org/10.1016/j.molstruc.2009.06.010

[15]. Chevallier, F.; Halauko, Y. S.; Pecceu, C.; Ibrahim, F. N.; Dam, T. U.; Thierry, R.; Vadim, E. M.; Oleg, A. I.; Florence, M. Org. Biomolec. Chem. 2011, 9(12), 4671-4683.
https://doi.org/10.1039/c1ob05267e

[16]. Alasalvar, C.; Soylu, M. S.; Unver, H.; Iskeleli, N. O.; Yildiz, M.; Ciftci, M.; Banoglu, E. Spectrochim. Acta A 2014, 132(11), 555-562.
https://doi.org/10.1016/j.saa.2014.05.014

[17]. Sheela, G. E.; Manimaran, D.; Joe, I. H.; Rahim, S.; Jothy, V. B. Spectrochim. Acta A 2015, 143, 40-48.
https://doi.org/10.1016/j.saa.2015.02.038

[18]. Eweiss, N. F.; Osman, A. J. Heterocycl. Chem. 1980, 17, 1713-1717.
https://doi.org/10.1002/jhet.5570170814

[19]. Dieckmann, W.; Platz, O. Chem. Ber. 1906, 38, 2989-2892.

[20]. Wolkoff, P. Can. J. Chem. 1975, 53, 1333-1335.
https://doi.org/10.1139/v75-183

[21]. Shanthan, R. P.; Venkataratnam, R. V. Tetrahedron Lett. 1991, 32, 5821-5825.
https://doi.org/10.1016/S0040-4039(00)93564-0

[22]. Fleming, I., Frontier Orbitals, and Organic Chemical Reactions, Wiley, London, 1976.

[23]. John, N. L.; Justo, C.; Jorge, T.; Christopher, G. Acta Cryst. E 2006, 62, o4930-o4932.
https://doi.org/10.1107/S1600536806034283

[24]. Xiao, H.; Tahir, K. J.; Goddard, I, W. A. J. Phys. Chem. Lett. 2011, 2, 212-217.
https://doi.org/10.1021/jz101565j

[25]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5651.
https://doi.org/10.1063/1.464913

[26]. Muscat, J.; Wander, A.; Harrison, N. M. Chem. Phys. Lett. 2001, 342, 397-401.
https://doi.org/10.1016/S0009-2614(01)00616-9

[27]. Bellamy, L. J. The infrared spectra of Complex Molecules, John Wiley and Sons, New York, Vol. 1 (3rd Edit. ), 1975, pp. 433.

[28]. Mansour, A. M. Inorg. Chim. Acta 2013, 394, 436-445.
https://doi.org/10.1016/j.ica.2012.08.025

[29]. Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455-461.

[30]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Hratchian, X.; Li, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A. 1, Gaussian, Inc., Wallingford CT, 2009.

[31]. Al-Zaydi, K. M.; Borik, R. M.; Elnagdi, M. H. Green Chem. Lett. Rev. 2012, 5(3), 241-250.
https://doi.org/10.1080/17518253.2010.483602

[32]. Sawsan, A. F. Inter. J. Adv. Res. 2014, 2(12), 442-453.

[33]. Fukui, K., Berlin: Theory of orientation and stereoselection. Springer-Verlag, 1975.
https://doi.org/10.1007/978-3-642-61917-5

[34]. Fukui, K. Science 1982, 218, 747-754.
https://doi.org/10.1126/science.218.4574.747

[35]. Buyukuslu, H.; Akdogan, M.; Yildirim, G.; Parlak, C. Spectrochim. Acta A 2010, 75(4), 1362-1369.
https://doi.org/10.1016/j.saa.2010.01.003

[36]. Jadwiga, S.; Elzbieta, K. K.; Cecylia, L.; Niewiadomy, A. Indian J. Pharm. Sci. 2014, 76(4), 287-298.

Supporting Agencies

National Research Centre Egypt and Department of Chemistry, Cairo University, Egypt.
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/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 (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).