Acid Catalyzed One Pot Synthesis of Nitro Substituted Triazolopyrimidine Derivatives

Authors

  • Paresh Ladwa  Department of Chemistry, M.D. Science College, Porbandar, Gujarat, India
  • Dr. Jayesh J. Modha  Department of Chemistry, Shree H. N. Shukla College of Science, Rajkot, Gujarat, India

Keywords:

Pyrazolo[1,5-a]pyrimidine, Triazolo pyrimidine, Biological evaluation

Abstract

In this paper we have described the Acid catalyzed synthesis of nitro substituted triazolopyrimidine derivatives in moderate to good yield. The reaction of various substituted aldehydes with 1-(2-chlorophenyl)-2-nitroethanone as active methylene compound and 5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile afforded the triazolo pyrimidine derivatives in the presence acid and Methanol as a solvent. We have also optimized the reaction condition using the various solvent. We have confirmed the structure on the basis of IR, Mass, 1H NMR, 13C NMR spectroscopy and elemental analysis.

References

  1. PCT Int. Appl., 2007, WO 2007076092 A2 20070705.
  2. (a) Alexander, J. O.; Wheeler, G. R.; Hill, P. D.; Morris, M. P. Biochem. Pharmacol.1966, 15, 881; (b) Elion, G. B.; Callahan, S.; Nathan, H.; Bieher, S.; Rundles, R.W.; Hitchings, G. H. Biochem. Pharmacol. 1963, 12, 85; (c) Earl, R. A.; Pugmire, R. J.; Revanker, G. R.; Townsend, L. B. Org. Chem. 1975, 40, 1822.
  3. Novinson, T.; Bhooshan, B.; Okabe, T.; Revankar, G. R.; Wilson, H. R. J. Med. Chem. 1976, 19, 512.
  4. Senga, K.; Novinson, T.; Wilson, H. R. Med. Chem.1981, 24, 610.
  5. Suzuki, M.; Iwasaki, H.; Fujikawa, Y.; Sakashita, M.; Kitahara, M.; Sakoda, R. Med. Chem. Lett.2001, 11, 1285.
  6. Almansa, C. A.; Alberto, F.; Cavalcanti, F. L.; Gomez, L. A.; Miralles, A.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. Med. Chem. 2001, 44, 350.
  7. Novinson, T.; Hanson, R.; Dimmitt, M. K.; Simmon, L. N.; Robins, R. K.; O’Brien, D. E. Med. Chem.1974, 17, 645.
  8. (a) Chen, C.; Wilcoxen, K. M.; Huang, C. Q.; Xie, Y.-F.; McCarthy, J. R.;Webb, T. R.; Zhu, Y.-F.; Saunders, J.; Liu, X.-J.; Chen, T.-K.; Bozigian, H.; Grigoriadis, D. E. Med. Chem. 2004, 47, 4787; (b) Huang, C. Q.; Wilcoxen, K. M.; Grigoriadis, D. E.; McCarthy, J. R.; Chen, C. Bioorg. Med. Chem. Lett.2004, 14, 3943; (c) Chen, C.; Wilcoxen, K. M.; Huang, C. Q.; McCarthy, J. R.; Chen, T.; Grigoriadis, D. E. Bioorg. Med. Chem. Lett. 2004, 14, 3669; (d) Wustrow, D. J.; Capiris, T.; Rubin, R.; Knobelsdorf, A.; Akunne, H.; Davis, M. D.; MacKenzie, R.; Pugsley, T. A.; Zoski, K. T.; Heffner, T. G.; Wise, L. D. Bioorg. Med. Chem. Lett. 1998, 8, 2067.
  9. (a) Selleri, S.; Gratteri, P.; Costagli, C.; Bonaccini, C.; Costanzo, A.; Melani, F.; Guerrini, G.; Ciciani, G.; Costa, B.; Spinetti, F.; Martini, C.; Bruni, F. Bioorg. Med. Chem. 2005, 13, 4821; (b) Selleri, S.; Bruni, F.; Costagli, C.; Costanzo, A.; Guerrini, G.; Ciciani, G.; Costa, B.; Martini, C. Bioorg. Med. Chem. 2001, 9, 2661; (c) Selleri, S.; Bruni, F.; Costagli, C.; Costanzo, A.; Guerrini, G.; Ciciani, G.; Costa, B.; Martini, C. Med. Chem.1999, 7, 2705.
  10. Drizin, I.; Holladay, M. W.; Yi, L.; Zhang, H. Q.; Gopalakrishnan, S.; Gopalakrishnan, M.; Whiteaker, K. L.; Buckner, S. A.; Sullivan, J. P.; Carroll, W. A. Med. Chem. Lett. 2002, 12, 1481.
  11. Altenbach, R.J.; Black, L.A.; Chang, S.; Cowart, M.D.; Faghih, R.; Gfesser, G.A.; Ku, Y.; Liu, H.; Lukin, K.A.; Nersesian, D.L.; Pu, Y.; Curtis, M.P.. S. Patent Appl. 256,309, 2005. Chem. Abstr. 2005, 144, 36332.
  12. Kirkpatrick,W. E.; Okabe, T.; Hillyard, I.W.; Robin, R. K.; Dren, A. T. J. Med. Chem. 1977, 20, 386.

International Journal of Scientific Research in Science, Engineering and Technology

Downloads

Published

2017-10-31

Issue

Volume 3, Issue 6, September-October-2017

Section

Research Articles

License

Copyright (c) IJSRSET

Creative Commons License

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

How to Cite

[1]
Paresh Ladwa, Dr. Jayesh J. Modha, " Acid Catalyzed One Pot Synthesis of Nitro Substituted Triazolopyrimidine Derivatives , International Journal of Scientific Research in Science, Engineering and Technology(IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099, Volume 3, Issue 6, pp.1020-1026, September-October-2017.