An efficient one-pot and solvent-free synthesis of chromeno[2,3-d] pyrimidine derivatives: Microwave assisted reaction

Heterocycles

Volumn 81, Issue 5, 2010, Pages 1271-1278

  Zonouzi, Afsaneh ^a   Biniaza, Mojtaba ^a   Mirzazadeh, Roghieh ^a   Talebi, Merzieh ^a   Ng, Seik Weng ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79751496431     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-11929     Document Type: Article

References (38)

1. R. V. B. Orrum and M. Greep, Synthesis, 2003, 1471.
2. A. Domling and I. Ugi, Angew. Chem. Int. Ed., 2000, 39, 3168.
3. L. Weber, K. Illegen, and M. Almstetter, Synlett, 1999, 3, 366.
4. A. Loupy, Microwave in Organic Synthesis, Wiley-VCH, Weinheim, 2002, 147.
5. R. S. Varma, Green Chem., 1999, 1, 43.
6. C. O. Kappe, Angew. Chem. Int. Ed., 2004, 43, 6250.
7. P. Lidstrom, J. Tierney, B. Wathey, and J. Westman, Tetrahedron, 2001, 57, 9225.
8. K. Tanaka, Solvent-free Organic Synthesis, Ed.; Wiley-VCH: Weinheim, 2003, 4.
9. J. A. Hadfield, V. H. Pavlidis, P. J. Perry, and A. T. McGown, Anti-Cancer Drugs, 1999, 10, 591.
10. O. Bruno, C. Brullo, A. Ranise, S. Schenone, F. Bondavalli, E. Barocelli, V. Ballabeni, M. Chiavarini, M. Tognolini, and M. Impicciatore, Bioorg. Med. Chem. Lett., 2001, 11, 1397.
11. A. H. Bedair, N. A. El-Hady, M. S. A. El-Latif, A. H. Fakery, and A. M. El-Agrody, Il Farmaco., 2000, 55, 708.
12. Y. Dai, Y. Guo, R. R. Frey, Z. Ji, M. L. Curtin, A. A. Ahmed, D. H. Albert, L. Arnold, S. S. Carries, T. Barlozzari, J. L. Batch, J. J. Bouska, P. F. Bouquet, G. A. Cunha, K. B. Glaser, J. Guo, J. Li, P. A. Mariotte, K. C. Marsh, M. D. Monkey, L. J. Pease, K. D. Stewart, V. S. Stoll, P. Taping, N. Wistar, S. K. Davidson, and M. R. Michaelis, J. Med. Chem., 2005, 48, 6066.
13. G. L. Bundy, D. E. Ayer, L. S. Banitt, K. L. Belonga, S. A. Mizsak, J. R. Palmer, J. M. Tustin, J. E. Chin, E. D. Hall, K. L. Linseman, I. M. Richards, H. M. Sherch, F. F. Sun, P. A. Yonkers, P. G. Larson, J. M. Lin, G. E. Padbury, C. S. Aaron, and J. K. Mayo, J. Med. Chem., 1995, 38, 4161.
14. I. O. Donkor, H. Li, and S. F. Queener, Eur. J. Med. Chem., 2003, 38, 605.
15. M. N. Nasr and M. M. Gineinah, Arch. Pharm. Pharm. Med. Chem., 2002, 6, 289.
16. M. S. Papalardo, F. Vittorio, L. Pasquinucci, and E. Bousquet, Farmaco., 1989, 44, 483.
17. C. N. O'Callaghan, J. Chem. Soc., Perkin Trans. 1, 1980, 1335.
18. J. Světlik, F. Tureček, and V. Hanuš, J. Chem. Soc., Perkin Trans. 1, 1988, 2053.
19. A. M. El-Agrody, H. A. Emam, M. H. El-Hakim, M. S. Abd El-latif, and A. H. Fakery, J. Chem. Res. (S), 1997, 320.
20. S. A. S. Ghozlan and A. Z. A. Hassanien, Tetrahedron, 2002, 58, 9423.
21. N. Y. Gorobets, V. V. Abakumov, A. V. Borisov, and V. M. Nikitchenko, Chem. Heterocycl. Compd., 2004, 40, 334.
22. T. M. Abu-Elmaati, F. M. El-Taweel, S. M. El-Mougi, and A. G. A. Elagamey, J. Heterocycl. Chem., 2004, 41, 655.
23. H. Turki, S. Abid, Y. le Bigot, S. Fery-Forgues, and R. el Gharbi, Synth. Commun., 2004, 34, 3553.
24. A. M. El-Sayed, Phosphorus, Sulfur and Silicon, 2006, 181, 2709.
25. E. S. Kurbatov, Z. A. Starikova, V. V. Krasnikov, and V. V. Mezheritskii, Chem. Heterocycl. Compd., 2006, 42, 1366.
26. A. V. Borisov, S. G. Dzhavakhishvili, I. O. Zhuravel, S. M. Kovalenko, and V. M. Nikitchenko, J. Comb. Chem., 2007, 9, 5.
27. D. J. Blythin, M. S. Domalski, Y. C. Kim, J. Kuo, and J.-H. Liu, Heterocycles, 1981, 16, 203.
28. A. Sakurai and H. Midrokawa, J. Org. Chem., 1969, 34, 3612.
29. H. Meyer, Liebigs. Ann. Chem., 1979, 1291.
30. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice. Oxford University Press, New York. 1998.
31. A. Zonouzi, M. Sadeghi Googheri, and P. S. Miralinaghi, Org. Prep. Proced. Int., 2008, 40, 471.
32. A. Zonouzi, H. Rahmani, D. Kazemi, and Z. Izakian, J. Chem. Res., 2008, 222.
33. A. Zonouzi, D. Kazemi, and M. Nezamabadi, Org. Prep. Proced. Int., 2006, 38, 307.
34. A. Zonouzi, Z. Izakian, and M. Biniaz, Org. Prep. Proced. Int., 2009, 41, 543.
35. Crystallographic data for the structure of compound 4b reported in this paper have been deposited with the Cambridge Crystallographi Data Center as supplementary publication No. CCDC 747366. These data can be obtained free of charge via www.ccdc.com.ac.uk/data-request/cif
36. M. Costa, F. Areias, L. Abrunhosa, A. Venâncio, and F. Proença, J. Org. Chem., 2008, 73, 1954.
37. J. Volmajer, R. Toplak, I. Leban, and L. M. A. Marechal, Tetrahedron, 2005, 61, 7012.
38. The experiments were performed using a microwave oven (ETHOS 1600, Milestone) with a power of 600 W specially designed for organic synthesis.