European Journal of Chemistry

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

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Published: Mar 31, 2018
DOI: https://doi.org/10.5155/eurjchem.9.1.30-38.1675
Keywords:
Pyrazoles, Thiophene, 1, 3-Thiazoles, DFT calculation, 3, 4-Thiadiazole, Cyclohexylacetamide
Section
Research Article
Issue
Vol. 9 No. 1 (2018): March 2018
Dates
Received 2017-11-23
Accepted 2017-12-29
Published 2018-03-31
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Main Article Content

Asmaa Mahmoud Fahim
Department of Green Chemistry, National Research Center, Dokki, P.O. Box. 12622, Cairo, Egypt
https://orcid.org/0000-0002-0293-3491
Ahmad Mahmoud Farag
Chemistry Department, Faculty of Science, Cairo University, Giza, 12613, Egypt
https://orcid.org/0000-0003-4796-1266
Mohamed Rabie Shaaban
Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukkarramah, 21955, Kingdom of Saudi Arabia
Eman Ali Ragab
Chemistry Department, Faculty of Science, Cairo University, Giza, 12613, Egypt

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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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.

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National Research Centre Egypt and Department of Chemistry, Cairo University, Egypt.
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