Microwave-assisted, mild, facile, and rapid one-pot three-component synthesis of some novel pyrano[2,3-d]pyrimidine-2,4,7-triones

Tetrahedron Letters

Volumn 53, Issue 52, 2012, Pages 7056-7059

  Azzam, Sadeq Hamood Saleh ^a   Pasha, M A ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Aromatic aldehydes; Barbituric acid; K2CO3; Meldrums acid; Microwave reactor; Pyrano 2,3 d pyrimidine 2,4,7 triones

Indexed keywords

ACID; ALDEHYDE; BARBITURIC ACID; MELDRUMS ACID; POTASSIUM CARBONATE; PYRANO[2,3 D]PYRIMIDINE 2,4,7 TRIONE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; REACTION TIME;

EID: 84869488539     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.10.056     Document Type: Article

References (49)

1. A. Stadler, and C.O. Kappe J. Comb. Chem. 3 2001 624
2. P. Wipf, and A. Cunningham Tetrahedron Lett. 36 1995 7819
3. M.G. Valverde, D. Dallinger, and C.O. Kappe Synlett 2001 741 744
4. G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O'Reilly, J. Schwartz, and M.F. Malley J. Med. Chem. 35 1992 3254
5. A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C. DeBrosse, S. Mai, A. Truneh, D.J. Faulkner, B. Carte, A.L. Breen, R.P. Hertzberg, R.K. Johnson, J.W. Westley, and B.C.M. Potts J. Org. Chem. 60 1995 1182
6. I.S. Zorkun, S. Sarac, S. Celebi, and K. Erol Bioorg. Med. Chem. Lett. 14 2006 8582
7. C.O. Kappe Bioorg. Med. Chem. Lett. 10 2000 49 51
8. A. Studer, P. Jeger, P. Wipf, and D.P. Curran J. Org. Chem. 62 1997 2917
9. J.C. Barrow, P.G. Nantermet, H.G. Selnick, K.L. Glass, K.E. Rittle, K.F. Gilbert, G. Steele, C.F. Homnick, R.M. Freidinger, R.W. Ransom, P. Kling, D. Reiss, T.P. Brote, T.W. Schorn, R.S.L. Chang, S.S. O'Malley, T.V. Olah, J.D. Ellis, A. Barris, K. Kassahun, P. Leppert, D. Nagarathnam, and C. Forray J. Med. Chem. 4 2000 2703
10. C.O. Kappe Eur. J. Med. Chem. 35 2000 1043
11. K. Folker, and T.B. Johnson J. Am. Chem. Soc. 55 1933 3784
12. F. Sweet, and D. Fissekis J. Am. Chem. Soc. 95 1973 8741
13. S.V. Vdovina, and V.A. Mamedov Russ. Chem. Rev. 77 2008 1017
14. A.K. Sharma, S. Jayakumar, M.S. Hundal, and M.P. Mahajan J. Chem. Soc., Perkin Trans. 1 2002 774
15. S. Sasaki, N. Cho, Y. Nara, M. Harada, S. Endo, N. Suzuki, S. Furuya, and M. Fujino J. Med. Chem. 46 2003 113
16. L.H. Li, T.L. Wallace, K.A. Richard, and D.E. Tracey Cancer Res. 45 1985 532
17. S. Bartolini, A. Mai, M. Artico, N. Paesano, D. Rotili, C. Spadafora, and G. Sbardella J. Med. Chem. 48 2005 6776
18. A.S. Jones, J.R. Swgers, R.T. Walker, and E.D. Clercq J. Med. Chem. 31 1988 268
19. J.D. Brown A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry 1984 Pergamon Press Oxford 3 57
20. C. Heidelberger, and F. Arafield J. Cancer Res. 23 1963 1226 Chem. Abstr. 1964,60,2197
21. E.D. Clercq J. Med. Chem. 29 1988 1561
22. M. Baba, R. Pauvels, P. Herdwig, E.D. Clercq, J. Desmyster, and M. Vadepulfe Biochem. Biophys. Res. Commun. 142 1987 128
23. E.D. Clercq Anticancer Res. 6 1986 549
24. K. Hirota, K. Kubo, H. Sajiki, Y. Kitade, M. Sako, and Y. Maki J. Org. Chem. 62 1997 2999
25. D. Fenn The pyrimidines 1994 Wiley New York
26. D. Heber, C. Heers, and U. Ravens Pharmazie 48 1993 537
27. E.M. Grivasky, S. Lee, C.W. Sigal, D.S. Duch, and C.A. Nichol J. Med. Chem. 23 1980 327
28. A.D. Broom, J.L. Shim, and G.L. Anderson J. Org. Chem. 41 1976 1095
29. M.M. Ghorab, and A.Y. Hassan Phosphorus, Sulfur Silicon Relat. Elem. 141 1998 251
30. Furuya, S.; Ohtaki, T. Eur. Patent 6,085,65, 1994.
31. Coates, W. J. Eur. Patent 3,510,58, 1990.
32. Kitamura, N.; Onishi, A. Pyrimidopyrimidinedione derivatives and their use antiallergic agent. Eur. Patent 1,635,99, 1984.
33. J. Davoll, J. Clarke, and E.F. Elslager J. Med. Chem. 15 1972 837
34. Levitt, G, Herbicidal sulfonamides. U. S. Patent 4,339,267, 1982.
35. W.O. Foye Principidi Chemico Farmaceutica 1991 Piccin Padora, Italy
36. L.L. Andreani, and E. Lapi Bull. Chim. Farm. 99 1960 583
37. Y.L. Zhang, B.Z. Chen, K.Q. Zheng, M.L. Xu, X.H. Lei, and X.B. Yaoxue Chem. Abstr. 96 1982 135383e
38. L. Bonsignore, G. Loy, D. Secci, and A. ZCalignano Eur. J. Med. Chem. 28 1993 517
39. G.P. Ellis A. Weissberger, E.C. Taylor, The Chemistry of Heterocyclic Compounds Chromenes Chromanes and Chromones 1977 John Wiley New York 11 Chapter II
40. D. Arnesto, W.M. Horspool, N. Martin, A. Ramos, and C. Seaone J. Org. Chem. 54 1989 3069
41. A. Loupy Microwave in organic synthesis 2002 Wiley-VCH Weinheim
42. R.S. Varma Pure Appl. Chem. 13 2001 193
43. M.B. Madhusudana Reddy, and M.A. Pasha Synth. Commun. 2010 1895 40
44. M.A. Pasha, and V.P. Jayashankara Bioorg. Med. Chem. Lett. 17 2007 621
45. M.A. Pasha, and V.P. Jayashankara Indian J. Chem. 46B 2007 1328
46. M.A. Pasha, and V.P. Jayashankara J. Pharmacol. Toxicol. 1 2006 573
47. M.A. Pasha, and N. Aatika Synth. Commun. 40 2010 2864
48. M.B. Madhusudana Reddy, and M.A. Pasha Chin. Chem. Lett. 21 2010 1025
49. N. Aatika, and M.A. Pasha J. Sau. Chem. Soc. 15 2011 55