Synthesis and DFT study of novel pyrazole, thiophene, 1,3-thiazole and 1,3,4-thiadiazole derivatives-Reference-Cited by-同舟云学术

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

Published:2018-03-31 Issue:1 Volume:9 Page:30-38
ISSN:2153-2257
Container-title:European Journal of Chemistry
language:en
Short-container-title:Eur J Chem

Author:

Fahim Asmaa Mahmoud¹^ORCID,Farag Ahmad Mahmoud²^ORCID,Shaaban Mohamed Rabie³,Ragab Eman Ali²

Affiliation:

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

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.

Publisher

European Journal of Chemistry

Link

http://www.eurjchem.com/index.php/eurjchem/article/viewFile/1675/pdf_1675

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