European Journal of Chemistry

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



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Hafez Mohamed El-Shaaer

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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El-Shaaer, H. M. Cyclocondensation, Antimicrobial Activity and Semi-Empirical AM1-MO Calculations of Benzopyrone Derivatives. Eur. J. Chem. 2012, 3, 51-56.

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References

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

[2]. Periers, A. M.; Laurin, P.; Benedetti, Y.; Lachaud, S.; Ferroud, D.; Iltis, A.; Haesslein, J. L.; Klich, M.; LHermite, G.; Musicki, B. Tetrahedron Lett. 2000, 41(6), 867-871.
http://dx.doi.org/10.1016/S0040-4039(99)02177-2

[3]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z. Phosphorus Sulfur 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-Shaaer, H. M.; Foltinova, P.; Lacova, M.; Chovancova, J.; Stankovicova, H. Farmaco 1998, 53, 224-232
http://dx.doi.org/10.1016/S0014-827X(98)00015-9

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

[7]. Edwards, A. M.; Howell, J. B. L. Clin. Experim. Allergy 2000, 30, 756-774.
http://dx.doi.org/10.1046/j.1365-2222.2000.00879.x

[8]. 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

[9]. 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

[10]. Nawrot-Modranka, J.; Nawrot, E.; Graczyk, J. Eur. J. Med. Chem. 2006, 41, 1301-1309.
http://dx.doi.org/10.1016/j.ejmech.2006.06.004
PMid:16904795

[11]. Mao, P. C. M.; Mouscadet, J. F.; Leh, H.; Auclair, C.; Hsu, L. Y. Chem. Pharm. Bull. 2002, 50, 1634-1637
http://dx.doi.org/10.1248/cpb.50.1634

[12]. Kirkiacharian, S.; Thuy, D. T.; Sicsic, S.; Bakhchinian, R.; Kurkijan, R.; Tonnaire, T. Il Farmaco 2002, 57, 703-708.
http://dx.doi.org/10.1016/S0014-827X(02)01264-8

[13]. 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

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

[15]. 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

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

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