Issue

Vol. 26 No. 20 (2014)

Copyright (c) 2014 Nadia Ali Ahmed Elkanzi1

Creative Commons License

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

Synthesis of New Isolated Pyrazolo, Isoxazolo Derivatives Incorporating Pyrido[1,2]thiazinoquinoline

https://doi.org/10.14233/ajchem.2014.17177
Nadia Ali Ahmed Elkanzi1
1Chemistry Department, Faculty of Science, Aljouf University, Al Jouf 2014, Kingdom of Saudi Arabia 2Chemistry Department, Faculty of Science, Aswan University, Aswan 81528, Egypt *Corresponding author: Fax: +966 4 6247183; Tel: +966 4 6242271; E-mail: nadiaelkanzi88@yahoo.com

Corresponding Author(s) : Nadia Ali Ahmed Elkanzi1

Asian Journal of Chemistry, Vol. 26 No. 20 (2014)

Abstract

Acetylation of 7,14-diamino-5,5a,12,12a-tetrahydro-[1,2]thiazino[4',5':5,6]pyrido[2,3-g][1,2]thiazino[5,4-b]quinoline-1,6,8,13(2H,4H, 9H,11H)-tetraone (1) with acetic anhydride and glacial acetic acid gave 2,9-diacetyl-7,14-diamino-5,5a,6a,7,12,12a-hexahydro-[1,2]thiazino[4',5':5,6]pyrido[2,3-g][1,2]thiazino[5,4-b]quinoline-1,6,8,13(2H,4H,9H,11H)-tetraone (2) The one-pot reaction of compound (2) with the aromatic aldehydes (3a-c) in the presence of catalytic amount of piperidine gave the corresponding arylidene derivatives (4a-c). Reaction of the arylidene derivatives (4a-c) with an equimolar amount of hydrazine hydrate and/or phenylhydrazine in the presence of a base gave N-acetylpyrazolo-derivatives (5a-c) and N-phenylpyrazolo derivatives (6a-c). Similarly, the isooxazolo pyrimidine derivatives (7a-c) were obtained through the reaction of arylidene derivatives (4a-c) with an equimolar amount of hydroxylamine hydrochloride in ethanol in the presence of sodium hydroxide as a catalyst. The structures of the new compounds were elucidated by compatible analytical and spectroscopic measurements.

Keywords

Synthesis N-acetylpyrazolo N-phenylpyrazolo Arylidene Aromatic aldehydes.
Ali Ahmed Elkanzi1, N. (2014). Synthesis of New Isolated Pyrazolo, Isoxazolo Derivatives Incorporating Pyrido[1,2]thiazinoquinoline. Asian Journal of Chemistry, 26(20), 6874–6878. https://doi.org/10.14233/ajchem.2014.17177
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. T. Eicher and S. Hauptmann, The Chemistry of Heterocycles: Structure, Reactions, Syntheses and Applications, Wiley-VCH, edn. 2, ISBN 3527307206 (2003).
  2. J.T. John and J.J. Donald Jr. Rogier, both of St. Louis, Mo, G.D. Searle & Co., Skokie, Pt No: 5, 434, 178 (1995).
  3. I.V. Mashevskaya, S.V. Kol'tsova, E.V. Voronina, T.F. Odegova and A.N. Maslivets, Pharm. Chem. J., 35, 18 (2001).
  4. S.L. Janus, A.Z. Magdif, B.P. Erik and N. Claus, Chem. Eur. J., 130, 1167 (1999).
  5. H.J. Park, K. Lee, S. Park, B. Ahn, J.C. Lee, H.Y. Cho and K.I. Lee, Bioorg. Med. Chem. Lett., 15, 3307 (2005).
  6. I. Bouabdallah, L.A. M'Barek, A. Zyad, A. Ramdani, I. Zidane and A. Melhaoui, Nat. Prod. Res., 20, 1024 (2006).
  7. I. Yildirim, N. Ozdemir, Y. Akçamur, M. Dinçer and O. Andaç, Acta Crystallogr., E61, o256 (2005).
  8. D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice and M.E. Feigenson, J. Med. Chem., 28, 256 (1985).
  9. C.K. Chu and J. Cutler, J. Heterocycl. Chem., 23, 289 (1986).
  10. A.E.I. Amr GES, N. A. Abdel-Latif and M. M. Abdlla, Acta Pharm., 56, 1203 (2006).
  11. S. Chimichi, M. Boccalini, M.M.M. Hassan, G. Viola, F. Dall'Acqua and M. Curini, Tetrahedron, 62, 90 (2006).
  12. T.A. Henry, The Plant Alkoloids, Anmol Publication Pvt. Ltd. (1999).
  13. H. Kobayashi, M. Kato and F. Nitani, Chem. Abstr., 106, 297008/g (1989).
  14. R.A. Nugent, M. Murphy, S.T. Schlachter, C.J. Dunn, R.J. Smith, N.D. Staite, L.A. Galinet, S.K. Shields, D.G. Aspar, K.A. Richard and N.A. Rohloff, J. Med. Chem., 36, 134 (1993).
  15. M.A. Hantoon, Minnesota Med., 84, 102 (2001).
  16. X. Zhang, X. Li, G.F. Allan, T. Sbriscia, O. Linton, S.G. Lundeen and Z. Sui, J. Med. Chem., 50, 3857 (2007).
  17. N.M. Abunada, H.M. Hassaneen, N.G. Kandile and O.A. Miqdad, Mole-cules, 13, 1501 (2008).
  18. C.O. Wilson and O. Gisvold, Text book of Organic Medicinal and Pharma-ceutical Chemistry, Lippincott Williams & Wilkins Pitman, London (1966).
  19. K.-H. Wünsch and A.J. Boulton, J. Adv. Heterocycl. Chem., 8, 277 (1967).
  20. N.K. Kochetkov and S.D. Sokolov, Adv. Heterocycl. Chem., 2, 365 (1963).
  21. Y. Hasegawa and S. Michitaka, Jpn. Kokai Tokkyo Koho JP (1996).
  22. M. Suzuki and K. Nozaki, PCT Int. (1994).
  23. H. Takasugu, Kuno, atsushi, PCT Int. (1994).
  24. A.K. Benerjee and S. Bandyopadhyaya, Arzeim-Forschi, 44, 863 (1994).
  25. A. Zen and H. Kyoko, Jpn. Kokai Tokkyo Koho JP (1993).
  26. A. Zen and H. Kyoko, Jpn. Kokai Tokkyo Koho JP (1994).
  27. S. Ryng and D. Dec, Pharmazie, 49, 727 (1994).
  28. S.R. Modi and H.B. Naik, Oriental J. Chem., 10, 85 (1994).
  29. G. Habeeb, P.N.P. Rao and E.E. Knaus, Drug Dev. Res., 51, 273 (2000).
  30. G.E. Granero, M.M. de Bertorello and M.C. Brinón, J. Chem. Res. (S), 110 (1999).
  31. N.A.A. El Kanzi, Int. J. Org. Chem., 2, 352 (2012).
  32. P. Yeung, J. Hubbard, E. Korchinski and K. Midha, Eur. J. Clin. Pharmacol., 45, 563 (1993).
Read More
Author biographies is not available.
Download
Statistic
Read Counter : 0