European Journal of Chemistry 2012, 3(2), 172-178 | doi: https://doi.org/10.5155/eurjchem.3.2.172-178.582 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Hafez Mohamed El-Shaaer (1,*) , Salah Sayed Ibrahim (2) , Wafaa Ramzy Abd-Elmonem (3) , Christine Gamal Ibrahim (4)

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

Received: 29 Dec 2011 | Accepted: 20 Jan 2012 | Published: 30 Jun 2012 | Issue Date: June 2012

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


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).


Editor-in-Chief
European Journal of Chemistry

Keywords


Synthesis; α-Benzopyrone; Cyclocondensation; Antimicrobial activity; Chromeno[3,4-c]pyridinones; Molecular orbital calculations

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.3.2.172-178.582

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1517 times | icon graph PDF Article downloaded 753 times


Citations

/


[1]. 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
/


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


How to cite


El-Shaaer, H.; Ibrahim, S.; Abd-Elmonem, W.; Ibrahim, C. Eur. J. Chem. 2012, 3(2), 172-178. doi:10.5155/eurjchem.3.2.172-178.582
El-Shaaer, H.; Ibrahim, S.; Abd-Elmonem, W.; Ibrahim, C. An efficient cyclocondensation reactions, antimicrobial activity and molecular orbital calculations of α-benzopyrone derivatives. Eur. J. Chem. 2012, 3(2), 172-178. doi:10.5155/eurjchem.3.2.172-178.582
El-Shaaer, H., Ibrahim, S., Abd-Elmonem, W., & Ibrahim, C. (2012). An efficient cyclocondensation reactions, antimicrobial activity and molecular orbital calculations of α-benzopyrone derivatives. European Journal of Chemistry, 3(2), 172-178. doi:10.5155/eurjchem.3.2.172-178.582
El-Shaaer, Hafez, 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 [Online], 3.2 (2012): 172-178. Web. 23 Sep. 2023
El-Shaaer, Hafez, Ibrahim, Salah, Abd-Elmonem, Wafaa, AND Ibrahim, Christine. "An efficient cyclocondensation reactions, antimicrobial activity and molecular orbital calculations of α-benzopyrone derivatives" European Journal of Chemistry [Online], Volume 3 Number 2 (30 June 2012)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.3.2.172-178.582


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2012, 3(2), 172-178 | doi: https://doi.org/10.5155/eurjchem.3.2.172-178.582 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2023  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.