European Journal of Chemistry 2012, 3(1), 51-56. doi:10.5155/eurjchem.3.1.51-56.500

Cyclocondensation, antimicrobial activity and semi-empirical AM1-MO calculations of benzopyrone derivatives


Hafez Mohamed El-Shaaer (1,*)

(1) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt
(*) Corresponding Author

Received: 13 Aug 2011, Accepted: 22 Sep 2011, Published: 31 Mar 2012

Abstract


An efficient synthesis of 7-amino-9-hydroxy-6-oxo-6H-benzo[c]chromene-8-carbonitrile derivatives (2,6) and 4-methyl-2-oxo-2H-chromene-3-carbonitrile (5) via Claisen condensation of 2-hydroxyacetophenones (1,3) with ethyl cyanoacetate in the presence of sodium metal is reported. Reaction of 5 with thiosemicarbazide gave 1-(3-cyano-4-methyl-2-oxoquinolin-1(2H)-yl)thiourea (7). Treatment of 5 with 6,8-dichloro-4-oxo-4H-chromene-3-carboxaldehyde gave 4-(2-(6,8-dichloro-4-oxo-4H-chromen-3-yl)-2-hydroxyethyl)-2-oxo-2H-chromene-3-carbonitrile (9). Further treatment of 5 with ethyl acetate followed by condensation with 6,8-dichloro-3-formylchromone gave 7-((6,8-dichloro-4-oxo-4H-chromen-3-yl)methyleneamino)-9-hydroxy-6H-benzo[c]chromen-6-one (12). Structures of the products were established on the basis of elemental analysis, IR, 1H and 13C NMR, mass spectra and semi-empirical AM1-MO calculations. The antimicrobial activities of the synthesized products were also studied.

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Keywords


Synthesis; Benzopyrone; 4-Quinolinone; Cyclocondensation; AM1-MO calculation; Antimicrobial activity

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DOI: 10.5155/eurjchem.3.1.51-56.500

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Citations

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[1]. Hafez Mohamed El-Shaaer, Salah Sayed Ibrahim, Wafaa Ramzy Abd-Elmonem, Christine Gamal Ibrahim
An efficient cyclocondensation reactions, antimicrobial activity and molecular orbital calculations of α-benzopyrone derivatives
European Journal of Chemistry  3(2), 172, 2012
DOI: 10.5155/eurjchem.3.2.172-178.582
/


[2]. Hafez Mohamed El-Shaaer
An efficient synthesis of some new isolated and fused 2-oxo-2H-chromene derivatives as antimicrobial and antitumor agents
European Journal of Chemistry  4(2), 138, 2013
DOI: 10.5155/eurjchem.4.2.138-145.749
/


[3]. Vyacheslav Ya. Sosnovskikh, Vladislav Yu. Korotaev, Igor B. Kutyashev, Alexey Yu. Barkov, Alexander V. Safrygin
One-pot synthesis of functionalized benzo[c]coumarins and their precursors via the reaction of 2-(polyfluoroalkyl)chromones with 4-alkyl-3-cyanocoumarins
RSC Advances  6(63), 58188, 2016
DOI: 10.1039/C6RA12492E
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[4]. Tarik El-Sayed Ali, Magdy Ahmed Ibrahim, Nasser Mohamed El-Gohary, Azza Mohamed El‐Kazak
3-Formylchromones as diverse building blocks in heterocycles synthesis
European Journal of Chemistry  4(3), 311, 2013
DOI: 10.5155/eurjchem.4.3.311-328.815
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[5]. Adel Sayed Orabi, Sahar Said El-Sakka
Correlation between single crystal data and molecular mechanics calculation of 3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one
European Journal of Chemistry  10(2), 139, 2019
DOI: 10.5155/eurjchem.10.2.139-145.1838
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How to cite


El-Shaaer, H. Eur. J. Chem. 2012, 3(1), 51-56. doi:10.5155/eurjchem.3.1.51-56.500
El-Shaaer, H. Cyclocondensation, antimicrobial activity and semi-empirical AM1-MO calculations of benzopyrone derivatives. Eur. J. Chem. 2012, 3(1), 51-56. doi:10.5155/eurjchem.3.1.51-56.500
El-Shaaer, H. (2012). Cyclocondensation, antimicrobial activity and semi-empirical AM1-MO calculations of benzopyrone derivatives. European Journal of Chemistry, 3(1), 51-56. doi:10.5155/eurjchem.3.1.51-56.500
El-Shaaer, Hafez. "Cyclocondensation, antimicrobial activity and semi-empirical AM1-MO calculations of benzopyrone derivatives." European Journal of Chemistry [Online], 3.1 (2012): 51-56. Web. 19 Sep. 2019
El-Shaaer, Hafez. "Cyclocondensation, antimicrobial activity and semi-empirical AM1-MO calculations of benzopyrone derivatives" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

DOI Link: https://doi.org/10.5155/eurjchem.3.1.51-56.500

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