European Journal of Chemistry 2016, 7(3), 298-308 | doi: https://doi.org/10.5155/eurjchem.7.3.298-308.1447 | Get rights and content

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Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity


Mohamed Ahmed Mahmoud Abdel Reheim (1,*) , Ibrahim Saad Abdel Hafiz (2) , Safaa Mohamed (3)

(1) Department of Chemistry, Faculty of Science, Arish University, Arish 45511, Egypt
(2) Department of Chemistry, Faculty of Science, Arish University, Arish 45511, Egypt
(3) Department of Chemistry, Faculty of Science, Arish University, Arish 45511, Egypt
(*) Corresponding Author

Received: 10 May 2016 | Accepted: 11 Jun 2016 | Published: 30 Sep 2016 | Issue Date: September 2016

Abstract


A series of many important diverse number of fused heterocyclic systems were prepared from the reaction of 1-(2-hydroxynaphthalen-1-yl)-3-phenylpropane-1,3-dione with some bifunctional nucleophiles, these reactions mainly proceed via condensation of 1-(2-hydroxynaphthalen-1-yl)-3-phenylpropane-1,3-dione with the aldehydic function followed by nucleophilic attack. Structures of the new compounds were established by elemental analyses and spectral data. Some of the products were also screened in vitro for their antimicrobial activity.


Keywords


Pyrazole; Thiophene; β-Diketones; Dihydropyridine; Antimicrobial activity; Tetrahydropyrimidinethione

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DOI: 10.5155/eurjchem.7.3.298-308.1447

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Funding information


Department of Chemistry, Faculty of Science, Arish University, Arish, Egypt

Citations

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[1]. Ilya V Taydakov, Yuliya M Kreshchenova, Ekaterina P Dolotova
A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety
Beilstein Journal of Organic Chemistry  14, 3106, 2018
DOI: 10.3762/bjoc.14.290
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[2]. Mohamed Ahmed Mahmoud Abdel Reheim, Ibrahim Saad Abdel Hafiz, Ahmed Adel Mohamed Sarhan, Hala Mohamed Reffat
Synthesis and Biological Studies of Some New Pyrazole, Dihydropyridinethione, Pyrimidine, Thiophene and 4H-Pyran Derivatives
HETEROCYCLES  102(2), 291, 2021
DOI: 10.3987/COM-20-14354
/


[3]. Mohamed A. M. Abdel Reheim, Safaa M. Baker
Synthesis, characterization and in vitro antimicrobial activity of novel fused pyrazolo[3,4-c]pyridazine, pyrazolo[3,4-d]pyrimidine, thieno[3,2-c]pyrazole and pyrazolo[3′,4′:4,5]thieno[2,3-d]pyrimidine derivatives
Chemistry Central Journal  11(1), , 2017
DOI: 10.1186/s13065-017-0339-4
/


[4]. Pavel G. Sergeev, Valentin G. Nenajdenko
Recent advances in the chemistry of pyridazine — an important representative of six-membered nitrogen heterocycles
Russian Chemical Reviews  89(4), 393, 2020
DOI: 10.1070/RCR4922
/


[5]. Mohamed Ahmed Mahmoud Abdel Reheim, Ibrahim Saad Abdel Hafiz, Hend Saad Eldin Abdel Rady
Microwave assisted the short time clean synthesis of 1,3-diketones as building blocks in heterocyclic synthesis: a facile synthesis and antimicrobial evaluation of new dihydropyridine, 4H-pyrane, dihydropyridazine, pyrimidine and pyrazole derivatives
Molecular Diversity  , , 2021
DOI: 10.1007/s11030-020-10152-9
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How to cite


Reheim, M.; Hafiz, I.; Mohamed, S. Eur. J. Chem. 2016, 7(3), 298-308. doi:10.5155/eurjchem.7.3.298-308.1447
Reheim, M.; Hafiz, I.; Mohamed, S. Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity. Eur. J. Chem. 2016, 7(3), 298-308. doi:10.5155/eurjchem.7.3.298-308.1447
Reheim, M., Hafiz, I., & Mohamed, S. (2016). Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity. European Journal of Chemistry, 7(3), 298-308. doi:10.5155/eurjchem.7.3.298-308.1447
Reheim, Mohamed, Ibrahim Saad Abdel Hafiz, & Safaa Mohamed. "Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity." European Journal of Chemistry [Online], 7.3 (2016): 298-308. Web. 16 Apr. 2021
Reheim, Mohamed, Hafiz, Ibrahim, AND Mohamed, Safaa. "Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity" European Journal of Chemistry [Online], Volume 7 Number 3 (30 September 2016)

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