An Efficient Protocol for Acid-Amine Coupling using T3P as Coupling Agent

Authors

  • Arpit C. Radadia  Department of Chemistry, Saurashtra University, Rajkot, Gujarat, India
  • Jaydip G. Rajpara  
  • Rajendra Jadav  
  • Yogesh T. Naliapara  

Keywords:

Acid-Amine Coupling, T3P (Propylphosphonic Anhydride), Quinolone 4 Carboxylic Acid

Abstract

Amide bond is prevalent in peptides. Moreover, at least 25% pharmaceutical products also contain amide bond. Acid amine coupling of 4-(4-aminophenyl)morpholin-2-one with different acids has been synthesized in presence of T3P (Propylphosphonic anhydride), DIPEA base with Ethyl acetate as a solvent at room temperature for 30 mins to yield N-(4-(2-oxomorpholino)phenyl)-2-phenylquinoline-4-carboxamide derivatives.

References

  1. Abadi, A. H. ; Hegazy, G. H. ; El-Zaher, A. A. Bioorg. Med. Chem. 2005, 13 20), 5759.
  2. Larsen, R. D. ; Corley, E. G. ; King, A. O. ; Carroll, J. D. ; Davis, P. ; Verhoeven, T. R. ; Reider, P. J. ; Labelle, M. ; Gauthier, J. Y. ; Xiang, Y. Bin. J. Org. Chem. 1996, 61 10), 3398.
  3. Chen, Y. -L. ; Fang, K. -C. ; Sheu, J. -Y. ; Hsu, S. -L. ; Tzeng, C. -C. J. Med. Chem. 2001, 44 14), 2374.
  4. Braccio, R. G. Eur. J. Med. Chem 2000, 35, 1021.
  5. Kalluraya, B. ; Sreenivasa, S. Farm. 1998, 53 6), 399.
  6. Dubé, D. ; Blouin, M. ; Brideau, C. ; Chan, C. -C. ; Desmarais, S. ; Ethier, D. ; Falgueyret, J. -P. ; Friesen, R. W. ; Girard, M. ; Girard, Y. Bioorg. Med. Chem. Lett. 1998, 8 10), 1255.
  7. Ferrarini, P. L. ; Mori, C. ; Badawneh, M. ; Manera, C. ; Martinelli, A. ; Romagnoli, F. ; Saccomanni, G. ; Miceli, M. J. Heterocycl. Chem. 1997, 34 5), 1501.
  8. Maguire, M. P. ; Sheets, K. R. ; McVety, K. ; Spada, A. P. ; Zilberstein, A. J. Med. Chem. 1994, 37 14), 2129.
  9. Ko, T. -C. ; Hour, M. -J. ; Lien, J. -C. ; Teng, C. -M. ; Lee, K. -H. ; Kuo, S. -C. ; Huang, L. -J. Bioorg. Med. Chem. Lett. 2001, 11 3), 279.
  10. Nakatani, K. ; Sando, S. ; Saito, I. Bioorg. Med. Chem. 2001, 9 9), 2381.
  11. He, C. ; Lippard, S. J. Inorg. Chem. 2001, 40 7), 1414.
  12. Strigá?ová, J. ; Hudecova, D. ; Lásiková, A. ; Végh, D. Folia Microbiol. Praha). 2000, 45 4), 305.
  13. Michael, J. P. Nat. Prod. Rep. 2005, 22 5), 627.
  14. Michael, J. P. Nat. Prod. Rep. 2004, 21 5), 650.
  15. Xiang, Y. Y. ; Hill, J. M. ; Yu, G. ; Yang, Y. ; Kluge, A. F. ; Keith, D. ; Finn, J. ; Gallant, P. ; Silverman, J. ; Lim, A. Bioorg. Med. Chem. Lett. 2001, 11 4), 541.
  16. Gobec, S. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Thieme/Houben-Weyl Series, 2003; Vol. 16.
  17. Kim, S. Y. ; Park, K. H. ; Chung, Y. K. Chem. Commun. 2005, No. 10, 1321.
  18. Bassoude, I. ; Berteina-Raboin, S. ; Leger, J. -M. ; Jarry, C. ; Essassi, E. M. ; Guillaumet, G. Tetrahedron 2011, 67 12), 2279.
  19. Antoniotti, S. ; Duñach, E. Tetrahedron Lett. 2002, 43 22), 3971.
  20. Buu-Hoi, N. P. ; Xuong, N. D. ; Lavit, D. J. Org. Chem. 1953, 18 8), 910.
  21. Atwell, G. J. ; Baguley, B. C. ; Denny, W. A. J. Med. Chem. 1989, 32 2), 396.
  22. Allen, C. F. H. ; Spangler, F. W. ; Webster, E. R. J. Org. Chem. 1951, 16 1), 17.
  23. Attanasi, O. A. ; De Crescentini, L. ; Filippone, P. ; Foresti, E. ; Galezzi, R. ; Ghiviriga, I. ; Katritzky, A. R. Tetrahedron 1997, 53 15), 5617.
  24. Cho, C. S. ; Oh, B. H. ; Kim, J. S. ; Kim, T. -J. ; Shim, S. C. Chem. Commun. 2000, No. 19, 1885.
  25. Jiang, B. ; Si, Y. -G. J. Org. Chem. 2002, 67 26), 9449.
  26. Manske, R. H. F. ; Kulka, M. Org. React. 1953.
  27. Yadav, J. S. ; Reddy, B. V. S. ; Premalatha, K. Synlett 2004, 2004 6), 963.
  28. Thomas, A. ; Chakraborty, M. ; Ila, H. ; Junjappa, H. Tetrahedron 1990, 46 2), 577.
  29. Theoclitou, M. -E. ; Robinson, L. A. Tetrahedron Lett. 2002, 43 21), 3907.

International Journal of Scientific Research in Science, Engineering and Technology

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Published

2018-02-28

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Volume 4, Issue 1, January-February-2018

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Research Articles

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[1]
Arpit C. Radadia, Jaydip G. Rajpara, Rajendra Jadav, Yogesh T. Naliapara, " An Efficient Protocol for Acid-Amine Coupling using T3P as Coupling Agent , International Journal of Scientific Research in Science, Engineering and Technology(IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099, Volume 4, Issue 1, pp.84-87, January-February-2018.