Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Copyright (c) 2015 AJC

Creative Commons License

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

Synthesis and Identification of Some New 2,3-Disubstituted 1,3-Oxazepine-4,7-dione Derivatives Containing Azo Group and 1,3,4-Thiadiazole Moiety

https://doi.org/10.14233/ajchem.2015.18879
Zeid Hassan Abood
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq
Murtadha Mohammed Hussein
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq
Ihsan Mahdi Shaheed
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq

Corresponding Author(s) : Zeid Hassan Abood

zeid.ab2013@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8

Abstract

Azoaldehyde derivatives (1a-f) were prepared through coupling reactions between diazonium salts of six primary aromatic amines and alkaline solution of 2-hydroxy benzaldehyde. Compounds (1a-f) were then introduced in acid-catalyzed condensation reactions with 2-amino-5-mercapto-1,3,4-thiadiazole to obtain six new azoimines (2a-f). (2+5) Cycloaddition of (2a-f) with each maleic and phthalic anhydrides respectivily gave nine new oxazepines (3a-f) and (4b, 4d, 4e). The synthesized compounds might have some biological activity.

Keywords

1 3 4-Thiadiazole Azoimines (2 5) Cycloaddition 3-Oxazepine
Hassan Abood, Z., Mohammed Hussein, M., & Mahdi Shaheed, I. (2015). Synthesis and Identification of Some New 2,3-Disubstituted 1,3-Oxazepine-4,7-dione Derivatives Containing Azo Group and 1,3,4-Thiadiazole Moiety. Asian Journal of Chemistry, 27(8), 3074–3078. https://doi.org/10.14233/ajchem.2015.18879
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. C. Ma, S.J. Liu, L. Xin, J.R. Falck and D.S. Shin, Tetrahedron, 62, 9002 (2006); doi:10.1016/j.tet.2006.07.009.
  2. Y. Tang, J.C. Fettinger and J.T. Shaw, Org. Lett., 11, 3802 (2009); doi:10.1021/ol901018k.
  3. A.K.T. Mohammad, H. Osman and G.Y. Yeap, Int. J. Spectrosc., Article ID 945216 (2011); doi:10.1155/2011/945216.
  4. J.D. Moody, D. Zhang, T.M. Heinze and C.E. Cerniglia, Appl. Environ. Microbiol., 66, 3646 (2000); doi:10.1128/AEM.66.8.3646-3649.2000.
  5. S. Kapur, R. Cho, C. Jones, G. Mckay and R.B. Zipursky, Biol. Psychiatry, 45, 1217 (1999); doi:10.1016/S0006-3223(98)00204-2.
  6. H. Takeuchi, S. Yokota, S. Shimada, Y. Ohtani, S. Miura and H. Kubo, Curr. Res. Chin. Exp., 53, 427 (1993); doi:10.1016/S0011-393X(05)80202-4.
  7. Y. Ai, F. Song, S.T. Wang, Q. Sun and P. Sun, Mol. J., 15, 9364 (2010); doi:10.3390/molecules15129364.
  8. X. Liu, Y. Jia, B. Song, Z. Pang and S. Yang, Bioorg. Med. Chem. Lett., 23, 720 (2013); doi:10.1016/j.bmcl.2012.11.101.
  9. M.H. Serrano-Wu, D.R. St. Laurent, Y. Chen, S. Huang, K.-R. Lam, J.A. Matson, C.E. Mazzucco, T.M. Stickle, T.P. Tully, H.S. Wong, D.M. Vyas and B.N. Balasubramanian, Bioorg. Med. Chem. Lett., 12, 2757 (2002);doi:10.1016/S0960-894X(02)00529-2.
  10. F. Hamon, F. Djedaini-Pilard, F. Barbot and C. Len, Tetrahedron, 65, 10105 (2009); doi:10.1016/j.tet.2009.08.063.
  11. P.F. Gordon, The Chemistry and Applications of Dyes, In: Topics in Applied Chemistry, Plenum Press, New York, edn 3, p. 381 (1990).
  12. J.S. Malar and A.F. Reji, Int. J. Chem. Pharm. Sci., 3, 55 (2012).
  13. Swati, Ginni, R. Karnawat, I.K. Sharma and P.S. Verma, Int. J. Appl. Biol. Pharm. Technol., 2, 332 (2011).
  14. H. Xu and X. Zeng, Bioorg. Med. Chem. Lett., 20, 4193 (2010); doi:10.1016/j.bmcl.2010.05.048.
  15. M. Tonelli, I. Vazzana, B. Tasso, V. Boido, F. Sparatore, M. Fermeglia, M.S. Paneni, P. Posocco, S. Pricl, P.L. Colla, C. Ibba, B. Secci, G. Collu and R. Loddo, Bioorg. Med. Chem., 17, 4425 (2009); doi:10.1016/j.bmc.2009.05.020.
  16. M. Nikpour, S. Zarinabadi and S. Saberi, Bull. Chem. Soc. Ethiopia, 26, 115 (2012); doi:10.4314/bcse.v26i1.12.
  17. S.M. Alwan, Molecules, 17, 1025 (2012); doi:10.3390/molecules17011025.
  18. A.S. Mayhoub, L. Marler, T.P. Kondratyuk, E.J. Park, J.M. Pezzuto and M. Cushman, Bioorg. Med. Chem., 20, 2427 (2012); doi:10.1016/j.bmc.2012.01.047.
  19. A. Cansiz, A. Cetin, C. Orek, M. Karatepe, K. Sarac, A. Kus and P. Koparir, Mol. Biomol. Spectrosc., 97, 606 (2012); doi:10.1016/j.saa.2012.07.016.
  20. M.M. El-Sadek, S.Y. Hassan, H.E. Abdelwahab and G.A. Yacout, Molecules, 17, 8378 (2012); doi:10.3390/molecules17078378.
  21. F. Vergne, P. Bernardelli, E. Lorthiois, N. Pham, E. Proust, C. Oliveira, A. Mafroud, F. Royer, R. Wrigglesworth, J. Schellhaas, M. Barvian, F. Moreau, M. Idrissi, A. Tertre, B. Bertin, M. Coupe, P. Berna and P. Soulard, Bioorg. Med. Chem. Lett., 14, 4607 (2004); doi:10.1016/j.bmcl.2004.07.008.
  22. Y. Song, D.T. Connor, A.D. Sercel, R.J. Sorenson, R. Doubleday, P.C. Unangst, B.D. Roth, V.G. Beylin, R.B. Gilbertsen, K. Chan, D.J. Schrier, A. Guglietta, D.A. Bornemeier and R.D. Dyer, J. Med. Chem., 42, 1161 (1999); doi:10.1021/jm980570y.
  23. W.M. Xu, S.Z. Li, M. He, S. Yang, X.Y. Li and P. Li, Bioorg. Med. Chem. Lett., 23, 5821 (2013); doi:10.1016/j.bmcl.2013.08.107.
  24. A. Skrzypek, J. Matysiak, A. Niewiadomy, M. Bajda and P. Szymański, Eur. J. Med. Chem., 62, 311 (2013); doi:10.1016/j.ejmech.2012.12.060.
  25. Q.A. Acton, Azo Compounds: Advances in Research and Application, Scholarly Paper Edition, Atlanta, pp. 42-117 (2011).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 1 Download : 0