European Journal of Chemistry 2012, 3(2), 220-227 | doi: https://doi.org/10.5155/eurjchem.3.2.220-227.592 | Get rights and content

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Synthesis, structure characterization and biological evaluation of new 6,8-dichloro-2-methyl-4H-chromen-4-one derivatives


Marwa Sayed Salem (1,*) , Magda Ismail Marzouk (2) , Salma Nasser Ali (3) , Hassan Mohamed Fawzy Madkour (4)

(1) Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt
(2) Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt
(3) Chemistry Department, Faculty of Science, 7Th October University, Bani Walid, 2478, Libya
(4) Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt
(*) Corresponding Author

Received: 04 Feb 2012 | Accepted: 22 Mar 2012 | Published: 30 Jun 2012 | Issue Date: June 2012

Abstract


The typical active methyl functionality of 6,8-dichloro-2-methyl-4H-chromen-4-one is utilized to obtain 2-styrylchromones, pyruvate ester and phthalide via reactions with aromatic carboxaldehydes, diethyl oxalate and phthalic anhydride respectively. The phthalide provides illustrative example to convert a heterocyclic compound to an aliphatic one via the effect of alcoholic sodium methoxide. Bromination and cycloaddition reactions of 2-styrylchromones afford vicinal dibromide and adducts respectively. This work presents to the art a typical example of heterocyclic systems transformations through the conversion of the starting chromone to coumarin under the influence of thionyl chloride followed by aqueous potassium hydroxide. Some heterocyclic systems like pyrazole, isoxazol and quinolinone are obtained from the target chromone by treatment with hydrazines, hydroxylamine hydrochloride and ammonium acetate respectively. Thiation of starting chromone interestingly affords a dithiated product instead of the expected monothiated one. Antibacterial and antifungal activities of some synthesized compounds have been screened.

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Keywords


Thiation; 2-Styrylchromones; 2-Methylchromone; Diels-Alder reaction; Biological evaluation; Heterocyclic transformations

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DOI: 10.5155/eurjchem.3.2.220-227.592

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Funding information


Department of Chemistry, Faculty of Science, Ain Shams University, Egypt

Citations

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[1]. Marwa Sayed Salem, Maher Abd El-Aziz Mahmoud El-Hashash, Al-Shimaa Omar Ali Mahmoud, Hassan Mohamed Fawzy Madkour
Facile synthesis of new fused and non-fused heterocyclic systems from a γ-ketoacid
European Journal of Chemistry  5(1), 33, 2014
DOI: 10.5155/eurjchem.5.1.33-40.900
/

[2]. Eman A. El-Helw, Hamed A. Derbala, Manal M. El-Shahawi, Marwa S. Salem, Mamdouh M. Ali
Synthesis and In Vitro Antitumor Activity of Novel Chromenones Bearing Benzothiazole Moiety
Russian Journal of Bioorganic Chemistry  45(1), 42, 2019
DOI: 10.1134/S1068162019010047
/

[3]. Mounir Salem, Magda Marzouk, Azza El-Kazak
Synthesis and Characterization of Some New Coumarins with in Vitro Antitumor and Antioxidant Activity and High Protective Effects against DNA Damage
Molecules  21(2), 249, 2016
DOI: 10.3390/molecules21020249
/

[4]. Pooja Jindal, Rimpy Bhatia, Sadhika Khullar, Sanjay K. Mandal, Ramesh C. Kamboj
A green synthesis of thieno[2,3-c]xanthen-6-ones through the tandem photochemical sigmatropic shift and cyclization
Green Chemistry Letters and Reviews  7(2), 126, 2014
DOI: 10.1080/17518253.2014.898800
/

[5]. Marwa S. Salem, Sameh I. Sakr, Waled M. El-Senousy, Hassan M. F. Madkour
Synthesis, Antibacterial, and Antiviral Evaluation of New Heterocycles Containing the Pyridine Moiety
Archiv der Pharmazie  346(10), 766, 2013
DOI: 10.1002/ardp.201300183
/

[6]. Marwa S. Salem, Eman A. E. El-Helw, Hamed A. Y. Derbala
Development of Chromone–Pyrazole-Based Anticancer Agents
Russian Journal of Bioorganic Chemistry  46(1), 77, 2020
DOI: 10.1134/S1068162020010094
/

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How to cite


Salem, M.; Marzouk, M.; Ali, S.; Madkour, H. Eur. J. Chem. 2012, 3(2), 220-227. doi:10.5155/eurjchem.3.2.220-227.592
Salem, M.; Marzouk, M.; Ali, S.; Madkour, H. Synthesis, structure characterization and biological evaluation of new 6,8-dichloro-2-methyl-4H-chromen-4-one derivatives. Eur. J. Chem. 2012, 3(2), 220-227. doi:10.5155/eurjchem.3.2.220-227.592
Salem, M., Marzouk, M., Ali, S., & Madkour, H. (2012). Synthesis, structure characterization and biological evaluation of new 6,8-dichloro-2-methyl-4H-chromen-4-one derivatives. European Journal of Chemistry, 3(2), 220-227. doi:10.5155/eurjchem.3.2.220-227.592
Salem, Marwa, Magda Ismail Marzouk, Salma Nasser Ali, & Hassan Mohamed Fawzy Madkour. "Synthesis, structure characterization and biological evaluation of new 6,8-dichloro-2-methyl-4H-chromen-4-one derivatives." European Journal of Chemistry [Online], 3.2 (2012): 220-227. Web. 24 Jan. 2021
Salem, Marwa, Marzouk, Magda, Ali, Salma, AND Madkour, Hassan. "Synthesis, structure characterization and biological evaluation of new 6,8-dichloro-2-methyl-4H-chromen-4-one derivatives" European Journal of Chemistry [Online], Volume 3 Number 2 (30 June 2012)

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European Journal of Chemistry 2012, 3(2), 220-227 | doi: https://doi.org/10.5155/eurjchem.3.2.220-227.592 | Get rights and content

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