European Journal of Chemistry

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

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Published: Sep 30, 2015
DOI: https://doi.org/10.5155/eurjchem.6.3.305-313.1268
Keywords:
Oxidation, Flavanone, Isoflavone, Flavonoids, Benzofurans, Phenyliodonium diacetate
Section
Research Article
Issue
Vol. 6 No. 3 (2015): September 2015
Dates
Received 2015-04-28
Accepted 2015-06-08
Published 2015-09-30


Main Article Content

Huma Aslam Bhatti
Husein Ebrahim Jamal Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
Nizam Uddin
Husein Ebrahim Jamal Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
Khurshid Ayub
Department of Chemistry, Commission on Science and Technology for Sustainable Development in the South, Institute of Information Technology, Abbottabad, 22060, Pakistan
Bibi Saima
Department of Chemistry, Commission on Science and Technology for Sustainable Development in the South, Institute of Information Technology, Abbottabad, 22060, Pakistan
Maliha Uroos
Institute of Chemistry, University of the Punjab, Lahore, Punjab, 54590, Pakistan
Jamshed Iqbal
Centre for Advanced Drug Research, Commission on Science and Technology for Sustainable Development in the South, Institute of Information Technology, Abbottabad, 22060, Pakistan
Shazia Anjum
Cholistan Institute of Desert Studies, The Islamia University of Bahawalpur, 63100, Pakistan
Mark Edward Light
School of Chemistry, University of Southampton Highfield Campus, SO17 1BJ, Southampton, United Kingdom
Abdul Hameed
Husein Ebrahim Jamal Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
Khalid Mohammed Khan
Husein Ebrahim Jamal Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

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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Bhatti, H. A.; Uddin, N.; Ayub, K.; Saima, B.; Uroos, M.; Iqbal, J.; Anjum, S.; Light, M. E.; Hameed, A.; Khan, K. M. Synthesis, Characterization of Flavone, Isoflavone, and 2,3-Dihydrobenzofuran-3-Carboxylate and Density Functional Theory Studies. Eur. J. Chem. 2015, 6, 305-313.

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References

[1]. Ferreira, D.; Slade, D. Nat. Prod. Rep. 2002, 19, 517-541.
http://dx.doi.org/10.1039/b008741f

[2]. Corder, R.; Mullen, W.; Khan, N. Q.; Marks, S. C.; Wood, E. G.; Carrier, M. J.; Crozier, A. Nature 2006, 444, 566-566
http://dx.doi.org/10.1038/444566a

[3]. Keen, C. L. J. Am. Coll. Nutr. 2001, 20, 436S-439S.
http://dx.doi.org/10.1080/07315724.2001.10719181

[4]. Ferreira, D.; Li, X. C. Nat. Prod. Rep. 2000, 17, 193-212.
http://dx.doi.org/10.1039/a705728h

[5]. Tückmantel, W.; Kozikowski, A. P.; Romanczyk, L. J. J. Am. Chem. Soc. 1999, 121, 12073-12081.
http://dx.doi.org/10.1021/ja993020d

[6]. Kozikowski, A. P.; Tückmantel, W.; Böttcher, G.; Romanczyk, L. J. J. Org. Chem. 2003, 68, 1641-1658.
http://dx.doi.org/10.1021/jo020393f

[7]. Anderson, J. C.; Headley, C.; Stapleton, P. D.; Taylor, P. W. Tetrahedron 2005, 61, 7703-7711.
http://dx.doi.org/10.1016/j.tet.2005.05.086

[8]. Formica, J. V.; Regelson, W. Food Chem. Toxicol. 1995, 33, 1061-1080.
http://dx.doi.org/10.1016/0278-6915(95)00077-1

[9]. Green, N. S.; Foss, T. R.; Kelly, J. W. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 14545-14550.
http://dx.doi.org/10.1073/pnas.0501609102

[10]. Siddiqui, B. S.; Kardar, M. N.; Ali, S. T.; Khan, S. Helv. Chim. Acta 2003, 86, 2164-2169.
http://dx.doi.org/10.1002/hlca.200390174

[11]. Prakash, O.; Pahuja, S.; Moriarty, R. M. Synth. Commun. 1990, 20, 1417-1422.
http://dx.doi.org/10.1080/00397919008052857

[12]. Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 4, 221-227.
http://dx.doi.org/10.1055/s-1994-22803

[13]. Prakash, O.; Saini, N.; Sharma, P. K. Heterocycles 1994, 38, 409-431.
http://dx.doi.org/10.3987/REV-93-458

[14]. Meng, J.; Jiang, T.; Aslam Bhatti, H.; Siddiqui, B. S.; Dixon, S.; Kilburn, J. D. Org. Biomol. Chem. 2010, 8, 107-113.
http://dx.doi.org/10.1039/B918179B

[15]. Willgerodt, C. J. Prakt. Chem. 1886, 33, 154-160.
http://dx.doi.org/10.1002/prac.18860330117

[16]. Banks, D. F. Chem. Rev. 1966, 66, 243-266.
http://dx.doi.org/10.1021/cr60241a001

[17]. Zhdankin, V. V. Arkivoc 2009, 1, 1-62.

[18]. Richardson, R. D.; Wirth, T. Angew. Chem. Int. Ed. 2006, 45, 4402-4404.
http://dx.doi.org/10.1002/anie.200601817

[19]. Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
http://dx.doi.org/10.1080/00304949709355217

[20]. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
http://dx.doi.org/10.1021/cr010003+

[21]. Fulmer, G. R.; Miller, A. J.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176-2179.
http://dx.doi.org/10.1021/om100106e

[22]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
http://dx.doi.org/10.1063/1.464913

[23]. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
http://dx.doi.org/10.1103/PhysRevB.37.785

[24]. Ullah, H.; Shah, A. U. H. A.; Ayub, K.; Bilal, S. J. Phys. Chem. C 2013, 117, 4069-4078.
http://dx.doi.org/10.1021/jp311526u

[25]. Hashmi, M. A.; Khan, A.; Ayub, K.; Farooq, U. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 2014, 128, 225-214.
http://dx.doi.org/10.1016/j.saa.2014.02.163

[26]. Ullah, H.; Rauf, A.; Ullah, Z.; Fazli, S.; Anwar, M.; Shah, A. U. H. A.; Uddin, G.; Ayub, K. Spectrochim. Acta A 2014, 118, 210-214.
http://dx.doi.org/10.1016/j.saa.2013.08.099

[27]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Gaussian, Inc., Wallingford, CT, USA, 2009.

[28]. Duisenberg, A. J. J. Appl. Cryst. 1992, 25, 92-96.
http://dx.doi.org/10.1107/S0021889891010634

[29]. Hooft, R. COLLECT. Nonius BV, Delft, The Netherlands, 1998.

[30]. Otwinowski, Z.; Minor, W. Methods in Enzymology; In Macromolecular Crystallography, Part A; Jr, C. W. C., Sweet, R. M., Eds.; Academic Press: New York, 1997; vol. 276.

[31]. Sheldrick, G. M. Acta Cryst. A 1990, 46, 467-473.
http://dx.doi.org/10.1107/S0108767390000277

[32]. Sheldrick, G. M. SHELXL-97, University of Göttingen, Germany, 1997.

[33]. Watkin, D. M.; Pearce, L.; Prout, C. K. Chemical Crystallography Laboratory; University of Oxford, 1993.

[34]. Barros, A. I. R. N. A.; Silva, A. M. S.; Alkorta, I.; Elguero, J. Tetrahedron 2004, 60, 6513-6521.
http://dx.doi.org/10.1016/j.tet.2004.06.005

[35]. Tanaka, K.; Sugino, T. Green Chem. 2001, 3, 133-134.
http://dx.doi.org/10.1039/b101826b

[36]. Urgaonkar, S.; La Pierre, H. S.; Meir, I.; Lund, H.; RayChaudhuri, D.; Shaw, J. T. Org. Lett. 2005, 7, 5609-5612.
http://dx.doi.org/10.1021/ol052269z

[37]. Juhasz, L.; Szilagyi, L.; Antus, S.; Visy, J.; Zsila, F.; Simonyi, M. Tetrahedron 2002, 58, 4261-4265.
http://dx.doi.org/10.1016/S0040-4020(02)00360-5

[38]. Khanna, M. S.; Singh, O. V.; Garg, C. P.; Kapoor, R. P. Synth. Commun. 1993, 23, 585-590.
http://dx.doi.org/10.1080/00397919308009816

[39]. Zhang, Q.; Botting, N. P. Tetrahedron 2004, 60, 12211- 12216.
http://dx.doi.org/10.1016/j.tet.2004.10.028

[40]. Li, J. J. Name reactions: a collection of detailed mechanisms and synthetic applications, Springer Science & Business Media, 2010.

Supporting Agencies

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
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