Reactions of 6-aminouracils - A novel and highly efficient procedure for preparation of some new spiro pyridodipyrimidines under classical or microwave-assisted solvent-free conditions

Canadian Journal of Chemistry

Volumn 86, Issue 9, 2008, Pages 925-929

  Mohammadizadeh, Mohammad R ^a   Azizian, Javad ^b   Teimouri, Fatemeh ^e   Mohammadi, Ali A ^b   Karimi, Ali R ^d   Tamari, Esmail ^c  

^a PERSIAN GULF UNIVERSITY   (Iran)

^b SHAHID BEHESHTI UNIVERSITY   (Iran)

^c ISLAMIC AZAD UNIVERSITY   (Iran)

^d ARAK UNIVERSITY   (Iran)

^e PAYAME NOOR UNIVERSITY   (Iran)

Author keywords

1,3 dimethy1 6 aminouracil; Acenaphtoquinone; Isatin; Ninhydrin; Solvent free

Indexed keywords

1,3-DIMETHY1-6-AMINOURACIL; ACENAPHTOQUINONE; ISATIN; NINHYDRIN; SOLVENT-FREE;

SOLVENTS;

EID: 50849093252     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V08-117     Document Type: Article

References (50)

1. R.J. Ife, T.H. Brown, P. Blurton, D.J. Keeling, C.A. Leach, M.L. Meeson, and M.E. Parsons. J. Med. Chem. 38, 2763 (1995).
2. (a) M.L. Bourguet-Kondracki, M.T. Martin, and M. Guyot. Tetrahedron Lett. 37, 3457 (1996);
3. (b) M. Kobayashi, Y-J Chen, S. Aoki, Y. In, T. Ishida, and I. Kitagawa, Tetrahedron, 51, 3727 (1995);
4. (c) K.L. Rinehart, J. Kobayashi, G.C. Harbour, J. Gilmore, M. Mascal, T.G. Holt, L.S. Shield, and F. Lafargue. J. Am. Chem. Soc. 109, 3378 (1987);
5. (d) Y. Take, Y. Inouye, S. Nakamura, H.S. Allaudeen, and A.J. Kubo. Antibiot. 42, 107 (1989);
6. (e) S.E. Kane. Adv. Drug Res. 28, 181 (1996).
7. (a) A.S. Jones, J.R. Sayers, R.T. Walker, and E.J. De Clercq. J. Med. Chem. 31, 268 (1988);
8. (b) H. Griengl., E. Wanek, W. Schwarz, W. Streicher, B. Rosenwirth, and E. De Clercq. J. Med. Chem. 30, 1199 (1987);
9. (c) E. De Clercq and R. Bernaerts. J. Biol. Chem. 262, 14905 (1987);
10. (d) M. Baba, R. Pauwels, P. Herdewijn, De E. Clercq, J. Desmyter, and M. Vandeputte. Biochem. Biophys. Res. Commun. 142, 128 (1987);
11. (e) E. De Clercq. J. Med. Chem. 29, 1561 (1986);
12. (f) E. De Clercq. Anticancer Res. 6, 549 (1986).
13. (a) W.J. Coates. Eur. Patent 351-058. 1990;
14. (b) Chem. Abstr. 113, 40711 (1990);
15. (c) A.A. Ramsey. US Patent 3-830-812. 1974;
16. (d) Chem. Abstr. 81, 136174 (1974).
17. (a) E.C. Taylor, R.J. Knop, R.F. Meyer, A. Holmes, and M.L. Hoefle. J. Am. Chem. Soc. 82, 5711 (1960);
18. (b) J.D. Figueroa-Villar, C.L. Carneiro, and E.R. Cruz. Heterocycles, 34, 891 (1992).
19. N. Kitamura and A. Onishi. Eur. Pat. 163-599. 1984;
20. (b) Chem. Abstr. 104, 186 439 (1984).
21. (a) P. Raddatz and R. Bergmann. Ger. Patent 360-731. 1988;
22. (b) Chem. Abstr. 109, 54786 (1988).
23. (a) K. Singh, J. Sing, and H. Singh. Tetrahedron, 54, 935 (1998);
24. (b) D. Prajapati and A.J. Thakur. Tetrahedron Lett. 46, 1433 (2005);
25. (c) I. Devi, B.S.D. Kumar, and P.J. Bhuyan. Tetrahedron Lett. 44, 8307 (2003);
26. (d) D. Prajapati, M. Gohaina, and A. Thakur. J. Bioorg. Med. Chem. Lett. 16, 3537 (2006).
27. J. Azizian, M.R. Mohammadizadeh, F. Teimouri, A.A. Mohammadi, and A.R. Karimi. Synth. Commun. 36, 3631 (2006).
28. R.G. Pearson. J. Am. Chem. Soc. 85, 3533 (1963).
29. R.G. Pearson and J. Songstad. J. Am. Chem. Soc. 89, 1827 (1967).
30. J.L. Gazquez and F.J.J. Mendez. Phys. Chem. 98, 4049 (1994).
31. B. Tse-Lok. Chem. Rev. 75, 1 (1975).
32. O. Klopman. Chemical reactivity and reaction paths. John Wiley and Sons. New York. 1974.
33. O. Klopman. J. Am. Chem. Soc. 90, 223 (1968).
34. (a) D. Prajapatia and A. J. Thakur.Tetrahedron Lett. 46, 1433 (2005);
35. (b) J.L. Shim, R. Niess, and A.D. Broom. J. Org. Chem. 37, 578 (1972);
36. (c) D. Prajapati, M. Gohaina, and A. Thakur. Bioorg. Med. Chem. Lett. 16, 3537 (2006).
37. (a) I. Devi, B.S.D. Kumar, and P.J. Bhuyan. Tetrahedron Lett. 44, 8307 (2003)
38. (b) D.M. Volochnyuk, A.N. Koatyuk., A.M. Pinchuk, and A.A. Tolmachev.Tetrahedron Lett. 44, 391 (2003);
39. (c) S. Kumar, V. Kumar and S.S. Chimni. Tetrahedron Lett. 44, 2110 (2003).
40. (a) L. Perreux and A. Loupy. Tetrahedron, 57, 9199 (2001);
41. (b) S. Caddick. Tetrahedron, 51, 10403 (1995).
42. R.S. Varma. Green Chem. 1, 43 (1999).
43. (a) J. Azizian, A.R. Karimi, Z. Kazemizadeh, A.A. Mohammadi, and M.R. Mohammadizadeh. Tetrahedron Lett. 46, 6155 (2005);
44. (b) J. Azizian, A.R. Karimi, and A.A. Mohammadi. Synth. Commun. 33, 415 (2003);
45. (c) J. Azizian, A.R. Karimi, Z. Kazemizadeh, A.A. 'Mohammadi, and M.R. Mohammadizadeh. J. Org. Chem. 70, 1471 (2005).
46. (a) D.B. Hansen and M.M. Joullié. Chem. Soc. Rev. 34, 2005 (408);
47. (b) D.J. McCaldin. Chem. Rev. 60, 391(960).
48. (a) J.E. Dubois, M. El-Alaoui, and J. Toullec. J. Am. Chem. Soc. 103, 5393 (1980);
49. (b) Y. Zhu, G. Chuah, and S. Jaenicke. J. Catal. 227, 1 (2004);
50. (c) G. I. Nikishin and G.V. Somov. Russ. Chem. Bull. 14, 845 (1965).