European Journal of Chemistry 2015, 6(3), 305-313 | doi: https://doi.org/10.5155/eurjchem.6.3.305-313.1268 | Get rights and content

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Synthesis, characterization of flavone, isoflavone, and 2,3-dihydrobenzofuran-3-carboxylate and density functional theory studies


Huma Aslam Bhatti (1) , Nizam Uddin (2) , Khurshid Ayub (3) , Bibi Saima (4) , Maliha Uroos (5) , Jamshed Iqbal (6) , Shazia Anjum (7) , Mark Edward Light (8) , Abdul Hameed (9,*) , Khalid Mohammed Khan (10)

(1) Husein Ebrahim Jamal Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(2) Husein Ebrahim Jamal Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(3) Department of Chemistry, Commission on Science and Technology for Sustainable Development in the South, Institute of Information Technology, Abbottabad, 22060, Pakistan
(4) Department of Chemistry, Commission on Science and Technology for Sustainable Development in the South, Institute of Information Technology, Abbottabad, 22060, Pakistan
(5) Institute of Chemistry, University of the Punjab, Lahore, Punjab, 54590, Pakistan
(6) Centre for Advanced Drug Research, Commission on Science and Technology for Sustainable Development in the South, Institute of Information Technology, Abbottabad, 22060, Pakistan
(7) Cholistan Institute of Desert Studies, The Islamia University of Bahawalpur, 63100, Pakistan
(8) School of Chemistry, University of Southampton Highfield Campus, SO17 1BJ, Southampton, United Kingdom
(9) Husein Ebrahim Jamal Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(10) Husein Ebrahim Jamal Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(*) Corresponding Author

Received: 28 Apr 2015 | Revised: 08 Jun 2015 | Accepted: 08 Jun 2015 | Published: 30 Sep 2015 | Issue Date: September 2015

Abstract


We describe the oxidation of flavanones by employing phenyliodonium diacetate to form the flavone (15), isoflavone (8) and 2,3-dihydrobenzofurane (18) in this study. The oxidative method was found to be regioselective and dependent on the substitution pattern present on the two aromatic rings of the starting flavanone. The structures of products obtained were fully characterized by using IR, 1H and 13C NMR spectroscopy and Mass spectrometry. X-ray crystallography further confirms the structures of flavones and isoflavone. The density field theory calculations have also been performed to get more insight about the structures, electronic and spectroscopic properties of synthetic flavonoid derivatives. The geometrical parameters such as bond lengths and angels showed a good correlation with the values obtained through X-ray crystallography. Moreover, the theoretically simulated vibrational and UV-vis spectral values are in agreement with the experimental results.


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Keywords


Oxidation; Flavanone; Isoflavone; Flavonoids; Benzofurans; Phenyliodonium diacetate

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DOI: 10.5155/eurjchem.6.3.305-313.1268

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Funding information


Higher Education Commission, Pakistan and Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

Citations

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[1]. Ninh The Son, Dinh Thi Mai Thanh, Nguyen Van Trang
Flavone norartocarpetin and isoflavone 2′-hydroxygenistein: A spectroscopic study for structure, electronic property and antioxidant potential using DFT (Density functional theory)
Journal of Molecular Structure  1193, 76, 2019
DOI: 10.1016/j.molstruc.2019.05.016
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[2]. Suci Zulaikha Hildayani, Muhamad Abdulkadir Martoprawiro, Yana Maolana Syah
DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X Functional
Bulletin of Chemical Reaction Engineering & Catalysis  16(4), 796, 2021
DOI: 10.9767/bcrec.16.4.11487.796-803
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[3]. George Kwesiga, Alexandra Kelling, Sebastian Kersting, Eric Sperlich, Markus von Nickisch-Rosenegk, Bernd Schmidt
Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F
Journal of Natural Products  83(11), 3445, 2020
DOI: 10.1021/acs.jnatprod.0c00932
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[4]. Francisco Estévez-Sarmiento, Mercedes Said, Ignacio Brouard, Francisco León, Celina García, José Quintana, Francisco Estévez
3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells
Bioorganic & Medicinal Chemistry  25(21), 6060, 2017
DOI: 10.1016/j.bmc.2017.09.043
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[5]. Rajesh Kumar, Nitya Sharma, Om Prakash
Hypervalent Iodine Reagents in the Synthesis of Flavonoids and Related Compounds
Current Organic Chemistry  24(18), 2031, 2020
DOI: 10.2174/1385272824999200420074551
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[6]. George Kwesiga, Eric Sperlich, Bernd Schmidt
Scope and Applications of 2,3-Oxidative Aryl Rearrangements for the Synthesis of Isoflavone Natural Products
The Journal of Organic Chemistry  86(15), 10699, 2021
DOI: 10.1021/acs.joc.1c01375
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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Bhatti, H.; Uddin, N.; Ayub, K.; Saima, B.; Uroos, M.; Iqbal, J.; Anjum, S.; Light, M.; Hameed, A.; Khan, K. Eur. J. Chem. 2015, 6(3), 305-313. doi:10.5155/eurjchem.6.3.305-313.1268
Bhatti, H.; Uddin, N.; Ayub, K.; Saima, B.; Uroos, M.; Iqbal, J.; Anjum, S.; Light, M.; Hameed, A.; Khan, K. Synthesis, characterization of flavone, isoflavone, and 2,3-dihydrobenzofuran-3-carboxylate and density functional theory studies. Eur. J. Chem. 2015, 6(3), 305-313. doi:10.5155/eurjchem.6.3.305-313.1268
Bhatti, H., Uddin, N., Ayub, K., Saima, B., Uroos, M., Iqbal, J., Anjum, S., Light, M., Hameed, A., & Khan, K. (2015). Synthesis, characterization of flavone, isoflavone, and 2,3-dihydrobenzofuran-3-carboxylate and density functional theory studies. European Journal of Chemistry, 6(3), 305-313. doi:10.5155/eurjchem.6.3.305-313.1268
Bhatti, Huma, Nizam Uddin, Khurshid Ayub, Bibi Saima, Maliha Uroos, Jamshed Iqbal, Shazia Anjum, Mark Edward Light, Abdul Hameed, & Khalid Mohammed Khan. "Synthesis, characterization of flavone, isoflavone, and 2,3-dihydrobenzofuran-3-carboxylate and density functional theory studies." European Journal of Chemistry [Online], 6.3 (2015): 305-313. Web. 26 Sep. 2023
Bhatti, Huma, Uddin, Nizam, Ayub, Khurshid, Saima, Bibi, Uroos, Maliha, Iqbal, Jamshed, Anjum, Shazia, Light, Mark, Hameed, Abdul, AND Khan, Khalid. "Synthesis, characterization of flavone, isoflavone, and 2,3-dihydrobenzofuran-3-carboxylate and density functional theory studies" European Journal of Chemistry [Online], Volume 6 Number 3 (30 September 2015)

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