The synthesis of new pyrazolo[1,5-a]pyrimidine derivatives (original) (raw)

Abstract

A simple high-yielding procedure for the synthesis of novel pyrazolo[1,5-a]pyrimidine analogues is reported via the condensation of 1,3-diketones or keto ester with substituted 5aminopyrazoles in presence of H 2 SO 4 using AcOH as solvent.

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References (28)

  1. Bayomi, S. M.; Amin, K. M.; Al-obaid, A. M.; Hares, N. G. Egypt J. Pharm. Sci. 1993, 34, 117.
  2. Holla, B. S.; Kalluraya, B.; Sridhar, K. R.; Drake, E.; Thomas, L. M.; Bhandary, K. K.; Levine, M. J. Eur. Med. Chem. 1994, 29, 301. http://dx.doi.org/10.1016/0223-5234(94)90100-7
  3. Panisheva, E. R.; Kaplina, N. V.; Nikolaeva, I. S.; Phuskina, T. V.; Pershin Khim-Farm, Z. H. Chem. Abst. 1981, 15, 40.
  4. Abdou, I. M.; Saleh, A. M.; Zohdi, H. F. Molecule. 2004, 9, 109. http://dx.doi.org/10.3390/90300109
  5. Filler, R. Chem Technol. 1974, 4, 752. http://dx.doi.org/10.3390/90300109
  6. Moustafa, M. G.; Zeinab, H. I.; Soad, A. A. Heteroatom Chem. 2004, 1, 57. http://dx.doi.org/10.1002/hc.10212
  7. EI-Feky, A.; Abd-Ei-Samii, Z. K. Pharmazie 1996, 51, 540.
  8. Vijaya Raj, K. K.; Narayan, B. V.; Ashalatha, N.; Suchita, K. J. Pharmacol. Toxicol. 2006, 1, 559.
  9. Amin, M. A.; Iamil, M. M.; Addel, G. A.; Bauomy, A. H.; Ahmad, M. Alexandria J. Pharm. Sci. 2003, 17, 1.
  10. Lane, M. E.; Yu, B.; Rice, A.; Lipson, K. E.; Liang, C.; Sun, L.; Tang, C.; McMahon, G.; Pestell, R. G.; Wadler, S. Cancer Res. 2001, 61, 6170. http://cancerres.aacrjournals.org/content/61/16/6170
  11. Fraley, M. E.; Hoffman, W. F.; Rubino, R. S.; Hungate, R. W.; Tebben, A. J.; Rutledge, R. Z.; McFall, R. C.; Huckle, W. R.; Kendall, R. L.; Coll, K. E.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2002, 12, 2767. http://dx.doi.org/10.1016/S0960-894X(02)00525-5
  12. Fraley, M. E.; Rubino, R. S.; Hoffman, W. F.; Hambaugh, S. R.; Arrington, K. L.; Hungate, R. W.; Bilodeau, M. T.; Tebben, A. J.; Rutledge, R. Z.; Kendall, R. L.; McFall, R. C.; Huckle, W. R.; Coll, K. E.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2002, 12, 3537. http://dx.doi.org/10.1016/S0960-894X(02)00827-2
  13. Wu, Z.; Fraley, M. E.; Bilodeau, M. T.; Kaufman, M. L.; Tasber, E. S.; Balitza, A. E.; Hartman, G. D.; Coll, K. E.; Rickert, K.; Shipman, J.; Shi, B.; Sepp-Lorenzino, L.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2004, 14, 909. http://dx.doi.org/10.1016/j.bmcl.2003.12.007
  14. Arora, A.; Scholar, E. M. J. Pharmacol. Exp. Ther. 2005, 315, 971.
  15. Meijer, L.; Raymond, A. E. Acc. Chem. Res. 2003, 36, 417. http://dx.doi.org/10.1021/ar0201198
  16. Senga, K.; Novinson, T.; Wilson, H. R. J. Med. Chem. 1981, 24, 610. http://dx.doi.org/272 10.1021/jm00137a023
  17. Mukaiyama, H.; Nishimura, T.; Shiohara, H.; Kobayashi, S.; Komatsu, Y.; Kikuchi, S.; Tsuji, E.; Kamada, N.; Ohnota, H.; Kusama, H. Chem. Pharm. Bull. 2007, 55, 881. http://dx.doi.org/10.1002/chin.200748148
  18. Molla Ebrahimlo, A. R.; Khalafy, J.; Prager, R. H. Aust. J. Chem. 2009, 62, 126. http://dx.doi.org/10.1071/CH08370
  19. Molla Ebrahimlo, A. R.; Khalafy, J.; Poursattar Marjani, A.; Prager, R. H. Arkivoc 2009, xii, 17. http://dx.doi.org/10.3998/ark.5550190.0010.c03
  20. Poursattar Marjani, A.; Khalafy, J.; Chem. Heterocycl. Comp. 2011, 47, 96. http://dx.doi.org/10.1007/s10593-011-0725-0
  21. Poursattar Marjani, A.; Khalafy, J.; Molla Ebrahimlo, A. R. Synth. Commun. 2011, 41, 2475. http://dx.doi.org/10.1080/00397911.2010.505701
  22. Poursattar Marjani, A.; Khalafy, J.; Molla Ebrahimlo, A. R.; Prager, R. H. Bull. Korean. Chem. Soc. 2011, 32, 2183. http://dx.doi.org/10.5012/bkcs.2011.32.7.2183
  23. Poursattar Marjani, A.; Khalafy, J.; Prager, R. H. Chem. Heterocycl. Comp. 2012, 48, 931. http://dx.doi.org/10.1007/s10593-012-1079-y
  24. Khalafy, J.; Ezzati, M.; Rimaz, M.; Poursattar Marjani, A.; Yaghoobnejad Asl, H. J. Iran. Chem. Soc. 2014, 11, 1067. http://dx.doi.org/10.1007/s13738-013-0378-2
  25. Khalafy, J.; Etivand, N.; Dilmaghani, S.; Ezzati, M.; Poursattar Marjani, A. Tetrahedron Lett. 2014, 55, 3781. http://dx.doi.org/10.1016/j.tetlet.2014.05.073
  26. Perrin, D. D.; Armarego, W. L. F.; In Purification of Laboratory Chemicals, Pergamon Press: Oxford, U.K., 1988.
  27. Khalafy, J.; Poursattar Marjani, A.; Salami, F. Tetrahedron Lett. 2014, 55, 6671. http://dx.doi.org/10.1016/j.tetlet.2014.10.061
  28. Iwao, T.; Yasuo, S.; Yasunori, T.; Koji, N.; Hiroyuki: T.; JP. Patent 2005-162726, 2005 (CAS No. 824397-75-3).