Issue

Vol. 35 No. 3 (2023): Vol 35 Issue 3, 2023

Copyright (c) 2023 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Novel Isoxazoline/Isoxzolyl Pyrano Heterocyclic Annulated Flavones

https://doi.org/10.14233/ajchem.2023.27286
Rachakonda Sydhulua
Department of Chemistry, Nizam College, Osmania University, Hyderabad-500001, India
Yerrabelly Hemasria
Department of Chemistry, Nizam College, Osmania University, Hyderabad-500001, India

Corresponding Author(s) : Yerrabelly Hemasria

hemay2@yahoo.com

Asian Journal of Chemistry, Vol. 35 No. 3 (2023): Vol 35 Issue 3, 2023

Abstract

The synthesis of new isoxazoline/isoxazole pyrano fused flavone derivatives from 6-hydroxy 5-formyl flavone via in situ generation of nitrile oxide from aldoxime using ceric ammonium nitrate (CAN) as an oxidant followed by intramolecular cycloaddition reaction at olefin/alkyne functions is reported in high yields. The reaction involves regio selective annulation at C5/C6 position in preference to the C6/C7 position of flavones. All the synthesized compounds were successfully characterized by IR, 1H NMR, 13C NMR and ESI-MS.

Keywords

Flavone aldoximes Flavone-isoxazoline/isoxazole Ceric ammonium nitrate 1,3-Dipolar cycloaddition
Sydhulua, R., & Hemasria, Y. (2023). Synthesis of Novel Isoxazoline/Isoxzolyl Pyrano Heterocyclic Annulated Flavones. Asian Journal of Chemistry, 35(3), 624–628. https://doi.org/10.14233/ajchem.2023.27286
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. L. Wang, M. Chen, P.Y. Lam, F. Dini-Andreote, L. Dai and Z. Wei, Microbiome, 10, 233 (2022); https://doi.org/10.1186/s40168-022-01420-x
  2. A.N. Panche, A.D. Diwan and S.R. Chandra, J. Nutr. Sci., 5, e47 (2016); https://doi.org/10.1017/jns.2016.41
  3. J.B. Harborne and C.A. Williams, Phytochemistry, 55, 481 (2000); https://doi.org/10.1016/S0031-9422(00)00235-1
  4. M. Sajid, C.N. Channakesavula, S.R. Stone and P. Kaur, Biomolecules, 11, 754 (2021); https://doi.org/10.3390/biom11050754
  5. R.E. Mutha, A.U. Tatiya and S.J. Surana, Futur. J.Pharm. Sci., 7, 25 (2021); https://doi.org/10.1186/s43094-020-00161-8
  6. S. Ronsisvalle, F. Panarello, G. Longhitano, E.A. Siciliano, L. Montenegro and A. Panico, Cosmetics, 7, 71 (2020); https://doi.org/10.3390/cosmetics7030071
  7. T. Nagao, F. Abe, J. Kinjo and H. Okabe, Biol. Pharm. Bull., 25, 875 (2002); https://doi.org/10.1248/bpb.25.875
  8. M.-E.F. Hegazy, A.E.-H.H. Mohamed, A.M. El-Halawany, P.C. Djemgou, A.A. Shahat and P.W. Paré, J. Nat. Prod., 74, 937 (2011); https://doi.org/10.1021/np100378d
  9. R.S. Keri, S. Budagumpi, R.K. Pai and R.G. Balakrishna, Eur. J. Med. Chem., 78, 340 (2014); https://doi.org/10.1016/j.ejmech.2014.03.047
  10. V.M. Malikov and M.P. Yuldashev, Chem. Nat. Compd., 38, 358 (2002); https://doi.org/10.1023/A:1021638411150
  11. X. Wang, Z. Wang, P.S. Sidhu, R.U. Desai and Q. Zhou, PLoS One, 10, e0116409 (2015); https://doi.org/10.1371/journal.pone.0116409
  12. S. Burda and W. Oleszek, J. Agric. Food Chem., 49, 2774 (2001); https://doi.org/10.1021/jf001413m
  13. F. Trischitta and C. Faggio, Comp. Biochem. Physiol. C Toxicol. Pharmacol., 143, 17 (2006); https://doi.org/10.1016/j.cbpc.2005.11.012
  14. X. Wang, Y.Y. Ouyang, J. Liu and G. Zhao, Br. J. Nutr., 111, 1 (2014); https://doi.org/10.1017/S000711451300278X
  15. N. Agrawal and P. Mishra, Med. Chem. Res., 27, 1309 (2018); https://doi.org/10.1007/s00044-018-2152-6
  16. R. Brindabon and R.N. De, Monatsh. Chem, 141, 763 (2010); https://doi.org/10.1007/s00706-010-0323-3
  17. R.S.B. Gonçalves, M. Dos Santos, G. Bernadat, D. Bonnet-Delpont and B. Crousse, Beilstein J. Org. Chem., 9, 2387 (2003); https://doi.org/10.3762/bjoc.9.275
  18. K. Karthikeyan, T. Veenus Seelan, K.G. Lalitha and P.T. Perumal, Bioorg. Med. Chem. Lett., 19, 3370 (2009); https://doi.org/10.1016/j.bmcl.2009.05.055
  19. P. Poma, M. Notarbartolo, M. Labbozzetta, A. Maurici, V. Carina, A. Alaimo, M. Rizzi, D. Simoni and N. D’Alessandro, Int. J. Mol. Med., 20, 329 (2007).
  20. A. Alshamari, M. Al-Qudah, F. Hamadeh, L. Al-Momani, and S. AbuOrabi, Molecules, 25, 4271 (2020);
  21. https://doi.org/10.3390/molecules25184271
  22. A. Shaik, S. Kirubakaran and V. Thiruvemkatam, Acta Crystallogr. Sect. E Crystallogr. Commun., 73, 531 (2017); https://doi.org/10.1107/S2056989017003127
  23. P. Conti, G. Roda, H. Stabile, M.A. Vanoni, B. Curti and M. De Amici, Il Farmaco, 58, 683 (2003); https://doi.org/10.1016/S0014-827X(03)00107-1
  24. N.R. Sreenatha, B.N. Lakshminarayana, S. Madan Kumar, T.N. Mahadeva Prasad, K.S. Kiran, S. Vijay Shankar and K. Byrappa, Chem. Data Coll., 11-12, 131 (2017); https://doi.org/10.1016/j.cdc.2017.09.001
  25. A.G. Habeeb, P.N. Praveen Rao and E.E. Knaus, J. Med. Chem., 44, 2921 (2001); https://doi.org/10.1021/jm0101287
  26. N.R. Sreenatha, B.N. Lakshminarayana, D.P. Ganesha, C.R. Gnanendra, S. Nagaraju and S. Madan Kumar, Chem. Data Coll., 17-18, 394 (2018); https://doi.org/10.1016/j.cdc.2018.10.011
  27. T. Pinho e Melo, Curr. Org. Chem., 9, 925 (2005); https://doi.org/10.2174/1385272054 68420
  28. K.V. Gothelf and K.A. Jorgensen, Chem. Rev., 98, 863 (1998); https://doi.org/10.1021/cr970324e
  29. M.J. Raihan, V. Kavala, C.-W. Kuo, B.R. Raju and C.-F. Yao, Green Chem., 12, 1090 (2010); https://doi.org/10.1039/b926085d
  30. L. Tang, S. Zhang, J. Yang, W. Gao and J. Cui, Org. Prep. Proced. Int., 36, 453 (2004); https://doi.org/10.1080/00304940409356629
  31. Y.J. Rao, T. Sowjanya, G. Thirupathi, N.Y.S. Murthy and S.S. Kotapalli, Mol. Divers., 22, 803 (2018); https://doi.org/10.1007/s11030-018-9833-4
  32. S.S. Reddy, P. Sreenivas, Y.J. Rao and G.L.D. Krupadanam, ARKIVOC, 13, 55 (2009); https://doi.org/10.3998/ark.5550190.0010.d05
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 2 Download : 0