5-aminouracil as a building block in heterocyclic synthesis: Part I. One-pot synthesis of pyrimido[5,4-b]quinolin-2,4,9-triones under microwave irradiation without catalyst

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 63, Issue 12, 2008, Pages 1431-1437

  Shaker, Raafat M ^a   Abd Elrady, Mohamed ^a  

^a Minia University ^*  (Egypt)

Author keywords

5 aminouracil; Dimedone; Microwave irradiation; One pot synthesis; Pyrimido 5,4 b quinolin 2,4,9 triones

Indexed keywords

CATALYSTS; IRRADIATION; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POTASH;

5-AMINOURACIL; ANHYDROUS POTASSIUM CARBONATE; BUILDING BLOCKES; DIMEDONE; HETEROCYCLIC SYNTHESIS; ONE POT CONDENSATION; ONE-POT SYNTHESIS; PYRIMIDO[5,4-B]QUINOLIN-2,4,9-TRIONES;

SYNTHESIS (CHEMICAL);

EID: 58049179410     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2008-1215     Document Type: Article

References (44)

1. A. Dömling, Chem. Rev. 2006, 106, 17.
2. C. J. Li, Chem. Rev. 2005, 105, 3095.
3. C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51.
4. C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 24, 4957.
5. S. L. Cui, X. F. Lin, Y. G. Wang, J. Org. Chem. 2005, 70, 2866.
6. Y. J. Huang, F. Y. Yang, C. J. Zhu, J. Am. Chem. Soc. 2005, 127, 16386.
7. D. J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628;
8. Angew. Chem. Int. Ed. 2005, 44, 1602.
9. R. V. A. Orru, M. de Greef, Synthesis 2003, 1471.
10. E. S. H. El. Ashry, A. A. Kassem, ARKIVOC 2006, ix, 1.
11. C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957.
12. CO. Kappe, Angew. Chem. 2004, 116, 6408;
13. Angew. Chem. Int. Ed. 2004, 43, 6250.
14. A. R. Katritzky, S. K. Singh, ARKIVOC 2003, xiii, 68.
15. P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225.
16. A. A. Joshi, C. L. Viswanathan, Agent. Med. Chem. 2006, 5, 105.
17. A. A. Joshi, S. S. Narkhede, C. L. Viswanathan, Bioorg. Med. Chem. Lett. 2005, 15, 73.
18. A. Dlugosz, D. Dus, Farmaco 1996, 51, 364.
19. S. T. Sel vi, V. Nadaraj, S. Mohan, R. Sasi, M. Hema, Bioorg. Med. Chem. 2006, 14, 3896.
20. O. A. El-Sayed, T. M. Al-Turki, H. M. Al-Daffiri, B. A. Al-Bassam, M. E. Hussein, Boll. Chim. Farm. 2004, 143, 227.
21. V. K. Ahluwalia, B. Goyal, U. Das, J. Chem. Research (S) 1997, 266; (M) 1501.
22. H. A. Abdel Naby, R. A. Mekheimer, A. M. AbdElhameed, K. U. Sadek, J. Chem. Research (S) 1997, 678.
23. J. Quiroga, A. Hormaza, B. Insuasty, A. J. Ortiz, A. Sanchez, M. Nogueras, J. Heterocyclic Chem. 1998, 35, 231.
24. S. Tu, F. Fang, T. Li, S. Zhu, X. Zhang, J. Heterocyclic Chem. 2005, 42, 707.
25. S. M. Abdel-Gawad, M. S. A. El-Gaby, H. I. Heiba, H. M. Aly, M. M. Ghorab, J. Chin. Chem. Soc 2005, 52, 1227.
26. Y. M. Elkholy, M. A. Morsy, Molecules 2006, 11, 890.
27. J. Quiroga, S. Cruz, B. Insuasty, R. Abonía, M. Nogueras, J. Cobo, Tetrahedron Lett. 2006, 47, 27.
28. K. M. El-Shaieb, R. M. Shaker, A. A. Aly, Synth. Commun. 2008, 38, 2054.
29. R. M. Shaker, ARKIVOC 2006, xiv, 59.
30. R. M. Shaker, ARKIVOC 2006, xiv, 68.
31. A. A. ALy, A. A. Hassan, K. M. El-Shaieb, R. M. Shaker, Z. Naturforsch. 2005, 60b, 999.
32. R. M. Shaker, Heteroatom Chem. 2005, 16, 507.
33. R. M. Shaker, A. F. Mahmoud, F. F. Abdel-Latif, Phosphorus, Sulfur, Silicon and Relut. Elem. 2005, 180, 397.
34. A. A. Hassan, K. M. El-Shaieb, R. M. Shaker, D. Döpp, Heteroatom Chem. 2005, 16, 12.
35. R. M. Shaker, Phosphorus, Sulfur Silicon and Relat. Elem. 2003, 178, 1175.
36. R. M. Shaker, A. F. Mahmoud, F. F. Abdel-Latif, J. Chin. Chem. Soc: 2005, 52, 563.
37. R. M. Shaker, Phosphorus, Sulfur, Silicon and Relat. Elem. 2000, 158, 9.
38. R. M. Shaker, A. F. Mahmoud, F. F. Abdel-Latif, Phosphorus, Sulfur, Silicon and Relut. Elem. 2000, 160, 207.
39. N. Martin, M. Quinteiro, C Seoane, J. L. Soto, J. Heterocycl. Chem. 1996, 33, 45.
40. R. Alajarin, P. Jordan, J. J. Vaquero, J. Alvarez-Builla, Synthesis 1995, 389.
41. To be published separately. CCDC 678254 contains the supplementary crystallographic data for the structure determination of 6a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data.request/cif.
42. L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199.
43. P. Margaretha, O. E. Polansky, Monatsh. Chem. 1970, 101, 824.
44. M. L. Deb, P. J. Bhuyan, Tetrahedron Lett. 2005, 46, 6453.