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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, 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.
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DOI: 10.5155/eurjchem.9.1.30-38.1675
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Citations
[1]. Asmaa M. Fahim, Mona A. Shalaby
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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
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DOI: 10.1016/j.molstruc.2018.11.008
[3]. Asmaa M. Fahim, Ahmad M. Farag
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DOI: 10.1016/j.molstruc.2019.127025
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