One-Pot Green Method for the Synthesis of Oxazine Derivatives Under Aqueous Medium

Authors

  • Santosh R. Kshirsagar  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Ashok S. Pise  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Sagar I. Shinde  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Sandip P. Gondake  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Valmik S. Kapase  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India

DOI:

https://doi.org/10.32628/IJSRST207482

Keywords:

1, 3-oxazine derivatives, One-pot multicomponent condensation, Polyphosphoric acid, Aqueous medium, Green method.

Abstract

A simple, convenient, and environmentally friendly method for the synthesis of 1,3-oxazine derivatives has been developed under aqueous conditions. The reaction proceeds via one pot multicomponent condensation of ? or ?- naphthol, aromatic aniline and formaldehyde using polyphosphoric acid as green catalyst. The current protocols are simple, requires less reaction time and provides high yields. Non-polluting synthetic procedures are used to avoid harmful effects of organic solvents on the environment.

References

  1. P. Laszlo, Organic Reaction: Simplicity and Logic, Wiley New York, (1995).
  2. T. Tanaka, F. Toda Solvent-free Organic Synthesis, Chem, Rev.100, 1025-1074, (2000).
  3. M. Alam, R. Varala, S.R. AdapaSynlett, 67-70, (2003).
  4. A. Dondi, A. Massi, E. Minghini, S. Sabbatini, V. Bertoasi J. Org. Chem,68, 6172-6183, (2003).
  5. R. Hanselmann, J. C. Zhou, P. Ma, P. N. Confalone J. Org. Chem,68, 8739-8741, (2003).
  6. R. S. Thombal, V. H.Jadhav J. Chem. Appl. Biochem., 2,111 (2015).
  7. R. S.Thombal, Y. R. Lee, Org. Lett. 2018, 20, 4681.
  8. B. Ganem, Acc. Chem. Res., 42, 463, (2009).
  9. A. Domling, Chem. Rev., 106, 17, (2006).
  10. A. I. Domling, Ugi Angew, Chem. Int. Ed., 39, 3168, (2000).
  11. V.Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.Sreekanth, J. Mathen, A. Balagopal, Acc. Chem. Rev., 36, 899, (2003).
  12. S. L. Schreiber Science,287, 1964, (2000).
  13. L.A. Thompson, Curr. Opin. Chem. Biol., 4, 324, (2000).
  14. B. M. Trost, Angew. Chem. Int. Ed. Engl., 34, 259, (1995).
  15. L.F. Tietze Chem. Rev., 96, 115, (1996).
  16. B. M. Trost, Science,254, 1471, (1991).
  17. M. S. Singh, G. C. Nandi, S. Samai Green Chem.,14, 447, (2012).
  18. L. R. Wen, Z. R. Li, H. Cao. Green Chem., 14, 707, (2012).
  19. T. Kurz Tetrahedron, 61, 3091, (2005).
  20. A.I. Meyers, G. R. Malone, J. Org. Chem., 39, 618, (1974).
  21. A. I. Meyers, E. M. Smith J. Org. Chem., 37, 4289, (1972).
  22. M. Adib, E. Sheibani, K. Mostofi, K. Ghanbary, H. R. Bijanzadeh Tetrahedron, 62, 3435, (2006).
  23. N. Kajino, Y. Shibouta, K. Nishikawa, K. Meguro, Chem. Pharm. Bull., 11, 2896, (1991).
  24. Y. Katsura, S. Nishino, H. Takasugi, Chem. Pharm. Bull., 11, 2937, (1991).
  25. B. O. Buckman, R. Mohan, S. Koovakkat, Bioorg. Med. Chem. Lett., 8, 2235, (1998).
  26. H. V. Poel, G. Guilaumet, Viaud-Massuard, Tetrahedron Lett., 43, 1205, (2002).
  27. G. Mehdi, O. Abolfazl, R. M. Synth. Commun., 38, 4125, (2008).
  28. P. Zhang, E. A. Terefenko, A. Fensome, J. Wrobel, R. Winneker, Z. Zhang, Bioorg. Med. Chem. Lett., 13, 1313, (2003).
  29. F. A. Kerdesky, Tetrahedron Lett., 46, 1711, (2005).
  30. B. S. Holla, K. N. Poojary, B. S. Rao, M. K. Shivandana Eur. J. Med. Chem., 37, 511, (2002).
  31. G. Martin, R. A. Lahti, A.D. Rudzik, D. J. Duchamp, C. Chidester, T. J. Scahill,Med. Chem., 21, 542, (1978).
  32. G. Thomas, D. V. Mehta, R. Tahilramani, D. Joy, P. K. Talwalker, J. Med. Chem., 14, 335, (1971).
  33. B. S. Holla, K. N. Poojary, B. Kalluraya, P. V. Gowda II Farmaco, 51, 793, (1996).
  34. S. F. Wnuk, Tetrahedron, 49, 9877, (1993).
  35. A. A. Yuzhakov, Z. G. Chidgeavadze, R. S. Beabealashvilli FEBS, 306, 185, (1992).
  36. A. A. Yuzhakov, Z. G. Chidgeavadze, R. S. Beabealashvilli, A. A. Kraevskii, G. A. Galegov, M. N. Kornecva, D. N. Nosik, T. Y. Kilesso, Bioorg. Khim., 17, 504, (1991).
  37. L. Le Hir de Fallois, J. L. Decout, M. Fontecare, J. Chem. Soc. Perkin Trans, 17, 2587, (1997).
  38. M. Tomasulo, S. Sortino, F. M. Raymo, Org. Lett., 7, 1109, (2005).
  39. C. S. Higham, D. P. Dowling, J. L. Shaw, A. Cetin, C. J. Ziegler and J. R. Farrell, Tetrahedron Lett., 47, 4419, (2006).
  40. W. J. Burke, E. L. M. Glennie and C. Weatherbee, J. Org. Chem., 49, 909, (1964).
  41. P. M. Bijoy, K. Awanit, S. Satyasheel, P. K. Shukla and N. Mahendra, Eur. J. Med. Chem., 45, 1502, (2010).
  42. P. M. Bijoy and N. Mahendra, J. Heterocyclic Chem., 46, 1003, (2009).
  43. B. S. Suryakant, F. S. Kiran, B. S. Bapurao and S. S. Murlidhar, J. Koran Chem. Soci., 54, 437, (2010).
  44. I. Szatmari, F. Fulop,Curr. Org. Synth., 1, 155, (2004).
  45. I. Szatmari, F. Fulop, Tetrahedron, 69, 1255, (2013).
  46. R. Csutortoki, I. Szatmari, A. Koch, M. Heydenreich, I. Starke, F. Fulop, E. Kleinpeter, Tetrahedron, 68, 6284, (2012).
  47. S. A. Sadaphal, S. S. Sonar, K. F. Shelke, B. B. Shingate, M. S. Shingare Org. Commun., 3, 1, (2010).
  48. A. H. Kategaonkar, S. S. Sonar, B. B. Singate, M. S. Shingare, Green Chem. Lett. Rev., 3, 213, (2010).
  49. Z. Turgut, E. Pelit, A. Koycu, Molecules, 12, 345, (2007).
  50. H. Cao. H. F. Jiang, C. R. Qi, W. J. Yao, H. J. Chen, Tetrahedron Lett., 50, 1209, (2009).
  51. V. D. Dhakane etal, C. R. Chimie, 17, 431-436, (2014).
  52. F. Torav, G. Ochoa, Org. Lett., 2, 965, (2000).
  53. J. E. Kang, H. B. Kim, J. W. Lee, S. Shin, Org Lett., 8, 3537, (2006).
  54. M. Lei, L. Ma, I. Hu, Tetrahedron Lett., 50, 6393, (2009).
  55. Comprehensive Organic Synthesis Vol.2, 707-731, (1991).

Downloads

Published

2020-08-30

Issue

Section

Research Articles

How to Cite

[1]
Santosh R. Kshirsagar, Ashok S. Pise, Sagar I. Shinde, Sandip P. Gondake, Valmik S. Kapase "One-Pot Green Method for the Synthesis of Oxazine Derivatives Under Aqueous Medium" International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011,Volume 7, Issue 4, pp.332-339, July-August-2020. Available at doi : https://doi.org/10.32628/IJSRST207482