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Synthesis and DFT study of novel pyrazole, thiophene, 1,3-thiazole and 1,3,4-thiadiazole derivatives
Asmaa Mahmoud Fahim (1,*)
, Ahmad Mahmoud Farag (2) , 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 | Revised: 22 Dec 2017 | Accepted: 29 Dec 2017 | Published: 31 Mar 2018 | Issue Date: March 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.
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DOI: 10.5155/eurjchem.9.1.30-38.1675
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Funding information
National Research Centre Egypt and Department of Chemistry, Cairo University, Egypt.
Citations
[1]. Asmaa M. Fahim, Mona A. Shalaby
Synthesis, biological evaluation, molecular docking and DFT calculations of novel benzenesulfonamide derivatives
Journal of Molecular Structure 1176, 408, 2019
DOI: 10.1016/j.molstruc.2018.08.087
[2]. Ahmad M. Farag, Asmaa M. Fahim
Synthesis, biological evaluation and DFT calculation of novel pyrazole and pyrimidine derivatives
Journal of Molecular Structure 1179, 304, 2019
DOI: 10.1016/j.molstruc.2018.11.008
[3]. Asmaa M. Fahim, Ahmad M. Farag
Synthesis, antimicrobial evaluation, molecular docking and theoretical calculations of novel pyrazolo[1,5-a]pyrimidine derivatives
Journal of Molecular Structure 1199, 127025, 2020
DOI: 10.1016/j.molstruc.2019.127025
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DOI Link: https://doi.org/10.5155/eurjchem.9.1.30-38.1675
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European Journal of Chemistry 2018, 9(1), 30-38 | doi: https://doi.org/10.5155/eurjchem.9.1.30-38.1675 | Get rights and content
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