European Journal of Chemistry

An efficient cyclocondensation reactions, antimicrobial activity and molecular orbital calculations of α-benzopyrone derivatives



Main Article Content

Hafez Mohamed El-Shaaer
Salah Sayed Ibrahim
Wafaa Ramzy Abd-Elmonem
Christine Gamal Ibrahim

Abstract

An efficient synthesis of 4,6,8-trimethyl-2-oxo-2H-chromene-3-carbonitrile (2) via Claisen condensation of 3,5-dimethyl-2-hydroxyacetophenone with ethyl cyanoacetate in the presence of sodium metal is reported. Cyclocondensation reactions of compound (2) with ethyl acetate or with ethyl cyanoacetate in the presence of ethoxide gave sodium salt of 7-amino-9-hydroxy-2,4-dimethyl-6H-benzo[c]chromen-6-one derivatives (3) and (4) respectively, which upon neutralization with 10 % hydrochloric acid gave 7-amino-9-hydroxy-2,4-dimethyl-6H-benzo[c]chromen-6-one (5). Hydrolysis of compound (2) with ethanolic sodium hydroxide solution gave 4,6,8-trimethyl-2-oxo-2H-chromene-3-carboxylic acid (6). Treatment of compound (2) with Vilsmier reagent using excess POCl3 gave 4-(chloro(formyl)methyl-6,8-dimethyl-2-oxo-2H-chromene-3-carbonitrile (7). Also, conden-sation of compound (2) with DMF-DMA in xylene or with POCl3/DMF in pyridine gave the same product 4-((E)-2-(dimethylamino)vinyl)-6,8-dimethyl-2-oxo-2H-chromene-3-carbo-nitrile (8). The cyclocondensation reactions of compound (8) with hydroxylamine hydrochloride, urea, and with hydrazinecarbodithioic acid gave 3,4-dihydro-3-hydroxy-4-imino-7,9-dimethylchromeno[3,4-c]pyridin-5-one (9), 4-imino-7,9-dimethyl-5-oxo-4H-chro-meno[3,4-c]pyridine-3(5H)-carboxamide (10) and 3-amino-3,4-dihydro-4-imino-7,9-dimethyl chromeno[3,4-c]pyridin-5-one (11), respectively. Also, acid hydrolysis of compound (8) gave 7,9-dimethyl-3H-chromeno[3,4-c]pyridine-4,5-dione (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.

3_2_172_178_800


icon graph This Abstract was viewed 1676 times | icon graph Article PDF downloaded 844 times

How to Cite
(1)
El-Shaaer, H. M.; Ibrahim, S. S.; Abd-Elmonem, W. R.; Ibrahim, C. G. An Efficient Cyclocondensation Reactions, Antimicrobial Activity and Molecular Orbital Calculations of α-Benzopyrone Derivatives. Eur. J. Chem. 2012, 3, 172-178.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. El-Shaaer, H. M.; Abdel-Aziz, S. A.; Hanafy, F. I.; Ali, T. E.; El-Fauomy, A. Z. Eur. J. Chem. 2011, 2(2), 158-162.
http://dx.doi.org/10.5155/eurjchem.2.2.158-162.381

[2]. El-Shaaer, H. M. Eur. J. Chem. 2012, 3(1), 51-56.
http://dx.doi.org/10.5155/eurjchem.3.1.51-56.500

[3]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z. Phosphorus, Sulfur, and Silicon 2008, 183, 2139-2160.
http://dx.doi.org/10.1080/10426500701851291

[4]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z. Turk. J. Chem. 2008, 32, 365-374.

[5]. El-Sayed, A. M.; Abdallah, O. A. Phosphorus, Sulfur, and Silicon 2001, 170, 75-86.
http://dx.doi.org/10.1080/10426500108040586

[6]. El-Shaaer, H. M.; Foltinova, P.; Lacova, M.; Chovancova, J.; Stankovicova, H. Il Farmaco 1998, 53, 224-232.
http://dx.doi.org/10.1016/S0014-827X(98)00015-9

[7]. Gasparova, R.; Lacova, M.; El-Shaaer, H. M.; Odlerova, Z. Il Farmaco 1997, 52, 251-253.
PMid:9241831

[8]. Manolov, I.; Maichle-Moessmer, C.; Danchev, N. Eur. J. Med. Chem. 2006, 41, 882-890.
http://dx.doi.org/10.1016/j.ejmech.2006.03.007
PMid:16647160

[9]. Manolov, I.; Maichle-Moessmer, C.; Nicolova, I.; Danchev, N. Arch. Pharm. 2006, 336, 319-326.
http://dx.doi.org/10.1002/ardp.200500149
PMid:16649158

[10]. Jackson, S. A.; Sahni, S.; Lee, L.; Luo, Y.; Nieduzak, T. R. Bioorg. Med. Chem. 2005, 13, 2723-2739.
http://dx.doi.org/10.1016/j.bmc.2005.02.036

[11]. Choudhary, M.; Fatima, N.; Khan, K.; Jalil, S.; Iqbal, S.; Rahman, A. Bioorg. Med. Chem. 2006, 14, 8066-8072.
http://dx.doi.org/10.1016/j.bmc.2006.07.037

[12]. Cravotto, G.; Tagliapietra, S.; Cappelo, R.; Palmisano, G.; Curini, M.; Boccalini, M. Arch. Pharm. 2006, 336, 129-132.
http://dx.doi.org/10.1002/ardp.200500127
PMid:16511806

[13]. Ishar, M. P. S.; Singh, G.; Singh, S.; Sreenivasan, K. K.; Singh, G. Bioorg. Med. Chem. Lett. 2006, 16, 1366-1370.
http://dx.doi.org/10.1016/j.bmcl.2005.11.044

[14]. Liu, J.; Wu, J.; Zhao, Y. X.; Deng, Y. Y.; Mei, W. L.; Dai, H. F. Chin. Chem. Lett. 2008, 19, 934-936
http://dx.doi.org/10.1016/j.cclet.2008.05.034

[15]. Lacova, M.; Gasparova, R.; Kois, P.; Bohac, A.; El-Shaaer, H. M. Tetrahedron 2010, 66, 1410-1419.
http://dx.doi.org/10.1016/j.tet.2009.11.057

[16]. Gaplovsky, A.; Donovalova, J.; Lacova, M.; Mracnova, R.; El-Shaaer, H. M. J. Photochem. Photobiol. A 2000, 136, 61-65.
http://dx.doi.org/10.1016/S1010-6030(00)00319-1

[17]. El-Shaaer, H. M.; Perjessy, A.; Zahradnik, P.; Lacova, M.; Sustekova, Z. Monatsh. Chem. 1993, 124, 539-548.
http://dx.doi.org/10.1007/BF00819522

[18]. Bauer, A. W.; Kirby, W. W. M.; Sherris, J. C.; Turck, M. Am. J. Clin. Pathol. 1966, 45, 493-496.
PMid:5325707

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).