European Journal of Chemistry 2018, 9(1), 30-38. doi:10.5155/eurjchem.9.1.30-38.1675

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


Asmaa Mahmoud Fahim (1,*) orcid , Ahmad Mahmoud Farag (2) orcid , Mohamed Rabie Shaaban (3) , Eman Ali Ragab (4)

(1) Department of Green Chemistry, National Research Center, Dokki, P.O. Box. 12622, Cairo, Egypt
(2) Chemistry Department, Faculty of Science, Cairo University, Giza, 12613, Egypt
(3) Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukkarramah, 21955, Kingdom of Saudi Arabia
(4) Chemistry Department, Faculty of Science, Cairo University, Giza, 12613, Egypt
(*) Corresponding Author

Received: 23 Nov 2017, Accepted: 29 Dec 2017, Published: 31 Mar 2018

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.


Keywords


Pyrazoles; Thiophene; 1,3-Thiazoles; DFT calculation; 1,3,4-Thiadiazole; Cyclohexylacetamide

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DOI: 10.5155/eurjchem.9.1.30-38.1675

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[2]. Ahmad M. Farag, Asmaa M. Fahim
Synthesis, biological evaluation and DFT calculation of novel pyrazole and pyrimidine derivatives
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[3]. Asmaa M. Fahim, Ahmad M. Farag
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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.


How to cite


Fahim, A.; Farag, A.; Shaaban, M.; Ragab, E. Eur. J. Chem. 2018, 9(1), 30-38. doi:10.5155/eurjchem.9.1.30-38.1675
Fahim, A.; Farag, A.; Shaaban, M.; Ragab, E. Synthesis and DFT study of novel pyrazole, thiophene, 1,3-thiazole and 1,3,4-thiadiazole derivatives. Eur. J. Chem. 2018, 9(1), 30-38. doi:10.5155/eurjchem.9.1.30-38.1675
Fahim, A., Farag, A., Shaaban, M., & Ragab, E. (2018). Synthesis and DFT study of novel pyrazole, thiophene, 1,3-thiazole and 1,3,4-thiadiazole derivatives. European Journal of Chemistry, 9(1), 30-38. doi:10.5155/eurjchem.9.1.30-38.1675
Fahim, Asmaa, Ahmad Mahmoud Farag, Mohamed Rabie Shaaban, & Eman Ali Ragab. "Synthesis and DFT study of novel pyrazole, thiophene, 1,3-thiazole and 1,3,4-thiadiazole derivatives." European Journal of Chemistry [Online], 9.1 (2018): 30-38. Web. 21 Oct. 2019
Fahim, Asmaa, Farag, Ahmad, Shaaban, Mohamed, AND Ragab, Eman. "Synthesis and DFT study of novel pyrazole, thiophene, 1,3-thiazole and 1,3,4-thiadiazole derivatives" European Journal of Chemistry [Online], Volume 9 Number 1 (31 March 2018)

DOI Link: https://doi.org/10.5155/eurjchem.9.1.30-38.1675

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