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Journal of Chemistry
Volume 2013 (2013), Article ID 327095, 7 pages
http://dx.doi.org/10.1155/2013/327095
Research Article

Synthesis of New Pyrazolo[1,5-a]pyrimidine, Triazolo[4,3-a]pyrimidine Derivatives, and Thieno[2,3-b]pyridine Derivatives from Sodium 3-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-olate

Abdou O. Abdelhamid and Sobhi M. Gomha

Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

Received 30 May 2013; Revised 1 October 2013; Accepted 2 October 2013

Academic Editor: Bhimapaka C. Raju

Copyright © 2013 Abdou O. Abdelhamid and Sobhi M. Gomha. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. A. M. Kamal El-Dean, A. M. Elkhawaga, S. M. Radwan, and M. M. Ahmed, “Synthesis of some pyridothienopyrazolopyrimidopyrimidine and mercaptomethylpyrazolopyrimidine derivatives,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 184, no. 8, pp. 2034–2048, 2009. View at Publisher · View at Google Scholar · View at Scopus
  2. M. Ge, E. Cline, and L. Yang, “A general method for the preparation of 3-acyl-4-cyano-5-amino-pyrazoles,” Tetrahedron Letters, vol. 47, no. 32, pp. 5797–5799, 2006. View at Publisher · View at Google Scholar · View at Scopus
  3. H. A. El-Sherief, A. M. Mahmoud, and A. A. Ismaiel, “Studies on the synthesis and cyclization reactions of 2-(5-amino-3-arylpyrazol-1-yl)-3-methylquinoxalines,” Journal of Chemical Research S, no. 9, pp. 322–323, 1997. View at Google Scholar · View at Scopus
  4. A. A. Aly, “Synthesis of polyfunctionally substituted pyrazolonaphthyridine, pentaazanaphthalene, and heptaazaphenanthrene derivatives,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 181, no. 10, pp. 2395–2409, 2006. View at Publisher · View at Google Scholar · View at Scopus
  5. A. E. Rashad, M. I. Hegab, R. E. Abdel-Megeid, N. Fathalla, and F. M. E. Abdel-Megeid, “Synthesis and anti-HSV-1 evaluation of some pyrazoles and fused pyrazolopyrimidines,” European Journal of Medicinal Chemistry, vol. 44, no. 8, pp. 3285–3292, 2009. View at Publisher · View at Google Scholar · View at Scopus
  6. P. Sharma, N. Rane, and V. K. Gurram, “Synthesis and QSAR studies of pyrimido[4,5-d]pyrimidine-2,5-dione derivatives as potential antimicrobial agents,” Bioorganic & Medicinal Chemistry Letters, vol. 14, no. 16, pp. 4185–4190, 2004. View at Publisher · View at Google Scholar · View at Scopus
  7. O. Prakash, V. Bhardwaj, R. Kumar, P. Tyagi, and K. R. Aneja, “Organoiodine (III) mediated synthesis of 3-aryl/hetryl-5,7-dimethyl-1,2,4- triazolo[4,3-a]pyrimidines as antibacterial agents,” European Journal of Medicinal Chemistry, vol. 39, no. 12, pp. 1073–1077, 2004. View at Publisher · View at Google Scholar · View at Scopus
  8. M. Botta, M. Artico, S. Massa et al., “Synthesis, antimicrobial and antiviral activities of isotrimethoprim and some related derivatives,” European Journal of Medicinal Chemistry, vol. 27, no. 3, pp. 251–257, 1992. View at Publisher · View at Google Scholar · View at Scopus
  9. N. Agarwal, P. Srivastava, S. K. Raghuwanshi et al., “Chloropyrimidines as a new class of antimicrobial agents,” Bioorganic & Medicinal Chemistry, vol. 10, no. 4, pp. 869–874, 2002. View at Publisher · View at Google Scholar · View at Scopus
  10. R. A. Forsch, S. F. Queener, and A. Rosowsky, “Preliminary in vitro studies on two potent, water-soluble trimethoprim analogues with exceptional species selectivity against dihydrofolate reductase from Pneumocystis carinii and Mycobacterium avium,” Bioorganic & Medicinal Chemistry Letters, vol. 14, no. 7, pp. 1811–1815, 2004. View at Publisher · View at Google Scholar · View at Scopus
  11. N. Agarwal, S. K. Raghuwanshi, D. N. Upadhyay, P. K. Shukla, and V. J. Ram, “Suitably functionalised pyrimidines as potential antimycotic agents,” Bioorganic & Medicinal Chemistry Letters, vol. 10, no. 8, pp. 703–706, 2000. View at Publisher · View at Google Scholar · View at Scopus
  12. A. Agarwal, K. Srivastava, S. K. Puri, S. Sinha, and P. M. S. Chauhan, “A small library of trisubstituted pyrimidines as antimalarial and antitubercular agents,” Bioorganic & Medicinal Chemistry Letters, vol. 15, no. 23, pp. 5218–5221, 2005. View at Publisher · View at Google Scholar · View at Scopus
  13. T. J. Delia, M. Baumann, and A. Bunker, “Fused pyrimidines. Part 5. Pyrimido[4,5-d]pyrimidine analogues of folic acid,” Heterocycles, vol. 35, no. 2, pp. 1397–1410, 1993. View at Google Scholar · View at Scopus
  14. M. T. Cocco, C. Congiu, V. Lilliu, and V. Onnis, “Synthesis and in vitro antitumoral activity of new hydrazinopyrimidine-5- carbonitrile derivatives,” Bioorganic & Medicinal Chemistry, vol. 14, no. 2, pp. 366–372, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. V. Malik, P. Singh, and S. Kumar, “Unique chlorine effect in regioselective one-pot synthesis of 1-alkyl-/allyl-3-(o-chlorobenzyl) uracils: anti-HIV activity of selected uracil derivatives,” Tetrahedron, vol. 62, no. 25, pp. 5944–5951, 2006. View at Publisher · View at Google Scholar · View at Scopus
  16. X. Fan, X. Zhang, L. Zhou, K. A. Keith, E. R. Kern, and P. F. Torrence, “A pyrimidine-pyrazolone nucleoside chimera with potent in vitro anti-orthopoxvirus activity,” Bioorganic & Medicinal Chemistry Letters, vol. 16, no. 12, pp. 3224–3228, 2006. View at Publisher · View at Google Scholar · View at Scopus
  17. M. Botta, F. Occhionero, R. Nicoletti et al., “Synthesis and biological evaluation of 2-methoxy- and 2-Methylthio-6-[(2′-alkylamino)ethyl]-4(3H)-pyrimidinones with anti-rubella virus activity,” Bioorganic & Medicinal Chemistry, vol. 7, no. 9, pp. 1925–1931, 1999. View at Publisher · View at Google Scholar · View at Scopus
  18. R. Srivastava, A. Mishra, R. Pratap, D. S. Bhakuni, and R. C. Srimal, “Antithrombotic effect of thiopurinol,” Thrombosis Research, vol. 54, no. 6, pp. 741–749, 1989. View at Google Scholar · View at Scopus
  19. H. I. Skulnick, J. H. Ludens, M. G. Wendling et al., “Pyrimidinones. 3. N-substituted 6-phenylpyrimidinones and pyrimidinediones with diuretic/hypotensive and antiinflammatory activity,” Journal of Medicinal Chemistry, vol. 29, no. 8, pp. 1499–1504, 1986. View at Google Scholar · View at Scopus
  20. K. S. Atwal, B. N. Swanson, S. E. Unger et al., “Dihydropyrimidine calcium channel blockers. 3. 3-carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents,” Journal of Medicinal Chemistry, vol. 34, no. 2, pp. 806–811, 1991. View at Google Scholar · View at Scopus
  21. G. C. Rovnyak, K. S. Atwal, A. Hedberg et al., “Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents,” Journal of Medicinal Chemistry, vol. 35, no. 17, pp. 3254–3263, 1992. View at Google Scholar · View at Scopus
  22. G. J. Grover, S. Dzwonczyk, D. M. McMullen et al., “Pharmacologic profile of the dihydropyrimidine calcium channel blockers SQ 32,547 and SQ 32,946,” Journal of Cardiovascular Pharmacology, vol. 26, no. 2, pp. 289–294, 1995. View at Google Scholar · View at Scopus
  23. R. Jakše, J. Svete, B. Stanovnik, and A. Golobič, “Application of alkyl 3-dimethylamino-2-(1H-indol-3-yl)propenoates in the synthesis of 3-heteroarylindoles,” Tetrahedron, vol. 60, no. 21, pp. 4601–4608, 2004. View at Publisher · View at Google Scholar · View at Scopus
  24. M. R. Shaaban, T. M. A. Eldebss, A. F. Darweesh, and A. M. Farag, “A convenient synthesis of pyrazole-substituted heterocycles,” Journal of Chemical Research, vol. 34, no. 1, pp. 8–11, 2010. View at Publisher · View at Google Scholar · View at Scopus
  25. M. R. Shaaban, T. M. A. Eldebss, A. F. Darweesh, and A. M. Farag, “Synthesis of novel pyrazolo[3,4-d]pyridazine, pyrido[1,2-a]benzimidazole, pyrimido[1,2-a]benzimidazole and triazolo[4,3-a]pyrimidine derivatives,” Journal of Heterocyclic Chemistry, vol. 45, no. 6, pp. 1739–1744, 2008. View at Publisher · View at Google Scholar · View at Scopus
  26. S. A. Ahmed, A. M. Hussein, W. G. M. Hozayen, A. H. H. El-Ghandour, and A. O. Abdelhamid, “Synthesis of some pyrazolopyrimidines as purine analogues,” Journal of Heterocyclic Chemistry, vol. 44, no. 4, pp. 803–810, 2007. View at Google Scholar · View at Scopus
  27. A. O. Abdelhamid, E. K. A. Abdelall, N. A. Abdel-Riheem, and S. A. Ahmed, “Synthesis and antimicrobial activity of some new 5-arylazothiazole, pyrazolo[1,5-a] pyrimidine, [1,2,4]triazolo[4,3-a]pyrimidine, and pyrimido[1,2-a]benzimidazole derivatives containing the thiazole moiety,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 185, no. 4, pp. 709–718, 2010. View at Publisher · View at Google Scholar · View at Scopus
  28. A. O. Abdelhamid, S. A. Shokry, and S. M. Tawfiek, “A new approach for the synthesis of some pyrazolo [5,1-c]triazines and pyrazolo[1,5-a]pyrimidines containing naphtofuran moiety,” Journal of Heterocyclic Chemistry, vol. 49, no. 1, pp. 116–124, 2012. View at Publisher · View at Google Scholar · View at Scopus
  29. A. O. Abdelhamid, “Convenient synthesis of some new pyrazolo[1,5-a]pyrimidine, pyridine, thieno[2,3-b]pyridine, and isoxazolo[3,4-d]pyridazine derivatives containing benzofuran moiety,” Journal of Heterocyclic Chemistry, vol. 46, no. 4, pp. 680–686, 2009. View at Publisher · View at Google Scholar · View at Scopus