A Facile One-pot Synthesis of New Pyrazolopyrimidines and Pyrazolo Pyridines Derivatives
DOI:
https://doi.org/10.24297/jac.v8i1.6789Keywords:
substituted-5-amino-4-cyanopyrazoles, pyrazolo [3, 4-d] pyrimidines, pyrazolo [3, 4-b] pyridines, diethylmalonate, malononitrile and antibacterial activityAbstract
A Simple Facile One-pot reaction, novel and efficient rout for the synthesis of substituted pyrazolo [3, 4-d] pyrimidines, and pyrazolo [3, 4-b] pyridines, results from reaction of substituted-5-amino-4-cyanopyrazoles with malononitrile and diethylmalonate respectively. The structures of the products and conceivable mechanisms are discussed. The antibacterial activity of some new synthesized compounds was evaluated and seemed to be significant.
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References
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2. Kabayasahi, S. J. Pharm. Bull. 1973, 21, 941.
3. Novinson, T.; Dimmit, R. M. K.; Simon, I.N.; Robins, R. K.; Brien, D. E. O. J. Med. Chem. 1974, 17, 645.
4. Krikpatrick, W. E.; Okabe, T.; Hillyard, I. W.; Robins, R. K.; Dren, A. T.; Novinson, T. J. Med. Chem. 1977, 20, 386.
5. Elagamy, A. A.; El-Taweel, F. M. A.; Amer, F. A.; Zoorob, H. H. Arch. Pharm. (Weinhei) 1987, 320, 246.
6. (a) Kost, A. N.; Grandberg, I. I. In Advances in Heterocyclic Chemistry Katritzky, A.R. Ed. Academic Press: New York, 1996, p 347. (b) Nihset, H. B. J. Chem. Soc. 1938, 1568.
7. (a) Raiziss, G. W.; Clemence, L. W.; Friefelder, M. J. Am. Chem. Soc. 1941, 63, 2739. (b) Guarneri, M. Bull. Chim. Far. 1960, 99, 259. compounds – Pyrazolones
8. (a) Olah, G. A.; Iyer, P. S.; Prakash, S. Synthesis, 1982, 523. (b) Weisberger, A. “The Chemistry of Heterocyclic Pyrazolidones and derivativesâ€, New York, 1964; Vol. 20, pp 1 – 539.
9. (a) Hardy, C. R. Adv. Heterocycl. Chem. 1984, 36, 343. (b) Yu, G.; Mason, H.; Wu, X.; Wang, J.; Chong, S.; Dorough, G.; Henwood, A.; Pongrac, R.; Seliger, L.; He, B.; Normandin, D.; Adam, L.; Krupinski, J.; Macor, J. J. Med. Chem. 2001, 44, 1025. (c) El-Ahl, A. A. S.; Metwally, M. A.; Amer, F. A. Boll. Chim. Farm. 1995, 7, 369.
10. (a) Bettinetti, L.; Schlotter, K.; Hübner, H.; Gmeiner, P. J. Med. Chem. 2002, 45, 4594. (b) Löber, S.; Hübner, H.; Utz, W.; Gmeiner, P. J. Med. Chem. 2001, 44, 2691. (c) Kuroda, S.; Akahane, A.; Itani, H.; Nishimura, S.; Durkin, K.; Tenda, Y.; Sakane, K. Bioorg. Med. Chem. 2000, 8, 55. (d) Johns, B. A.; Gudmundsson,; Turner, K. S. E. M.; Allen, S. H.; Samano, V. A.; Ray, J. A.; Freeman, G. A.; Boyd, F. L.; Sexton, C. J.; Selleseth, D. W.; Creech, K. L.; Moniri, K. R. Bioorg. Med. Chem. 2005, 13, 2397. (e) Gudmundsson, K. S.; Johns, B. A.; Wang, Z.; Turner, E. M.; Allen, S. H.; Freeman, G. A.; Jr, F. L. B.; Sexton, C. J.; Selleseth, D. W.; Monirib, K. R.; Creech, K. L. Bioorg. Med. Chem. 2005, 13, 5346.
11. (a) Hardy, C. R. Adv. Heterocycl Chem. 1984, 36, 343. (b) Orth, R. E. J. Pharm. Sci. 1968, 57, 537. (c) Elnagdi, M. H.; Elmoghayar, M. R. H.; Elgmeie, G. E. H. Adv. Heterocycl. Chem. 1987, 41, 319. (d) Elnagdi, M. H.; Elmoghayar, M. R. H.; Sadek, K. U. Adv. Heterocycl. Chem. 1990, 48, 223.
12. Chen, Y. L. International Patent WO9534563 A1, Chem. Abstr. 1995, 124, 232447.
13. Veronese, A. C.; Callegari, R.; Salah, S. A. Tin (VI) chloride-promoted reaction of b-dicarbonyl compounds with nitrile. Synthesis of aminopyridines and aminoquinolines. Tetrahedron. Lett. 1990, 31, 3485-3488.
14. Taylor, E. D.; Borror, A. L. The reaction of Nitriles with o-Aminonitriles: Aconvenient synthesis of fused 4-Aminopyrimidine. J. Org. Chem. 1961, 26, 4967-4974.
15. Smyrl, N. R.; Smithwick, R. W. Hydroxide-catalyzed synthesis of heterocyclic aromatic amine derivative from nitriles. J. Heterocyclic Chem. 1982, 19, 493–496.
16. Cheng, C. C.; Robins, R. K. Potential purine antagonists. VI. Synthesis of 1-Alkyland 1-Aryl-4-aubatituted pyrazolo[3,4-d]pyrimidines. J. Org. Chem. 1956; 21; 1240-1256.
17. Abdellatif, M. Salaheldin; Ana, M. F. Oliveira-Campos and LÃgia M. Rodrigues. Heterocyclic synthesis with nitriles: Synthesis of pyrazolopyrimidine and pyrazolopyridine derivatives An International Journal for Rapid Communication of Synthetic Organic Chemistry, 2009, 1186-1195.
18. El-Sayed, T. Eur. J. Med. Chem. 2009, 44, 4385-4392.
19. Ghorab, M. M.; Ragab, F. A. Alqasoumi, S. I.; Alafeefy, A. M.; Aboulmagd, S. A. 490 Eur. J. Med. Chem. 2010, 45, 171-178.
20. Abunada, N. M.; Hassaneen, H. M.; Kandile, N. G.; Miqdad, O. A. Molecules. 487, 2008, 13, 1501-1517.
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Published
2014-03-12
How to Cite
Ahmed, H. A. M. (2014). A Facile One-pot Synthesis of New Pyrazolopyrimidines and Pyrazolo Pyridines Derivatives. JOURNAL OF ADVANCES IN CHEMISTRY, 8(1), 1533–1538. https://doi.org/10.24297/jac.v8i1.6789
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