Chromeno[2,3-d]pyrimidine-triones synthesis by a three-component coupling reaction

Chemical and Pharmaceutical Bulletin

Volumn 58, Issue 4, 2010, Pages 516-520

  Ghahremanzadeh, Ramin ^a,b   Fereshtehnejad, Fatemeh ^a   Bazgir, Ayoob ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

^b AVICENNA RESEARCH INSTITUTE   (Iran)

Author keywords

3 dione; Aldehyde; Barbituric acid; Chromeno 2,3 d pyrimidine; Cyclohexane 1

Indexed keywords

ALCOHOL; ALDEHYDE; BARBITURIC ACID; CHROMENE DERIVATIVE; CHROMENO[2,3 D]PYRIMIDINE TRIONES; CYCLOHEXANE 1,3 DIONES; CYCLOHEXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; POLYMERIZATION; SYNTHESIS;

ALDEHYDES; BARBITURATES; BENZOPYRANS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLOHEXANONES; PYRIMIDINES;

EID: 77950818754     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.58.516     Document Type: Article

References (54)

1. Zhu J., Bienaymé H., "Multicomponent Reactions," Wiley-VCH, Weinheim, Germany, 2005.
2. Pandey G., Singh R. P., Gary A., Singh V. K., Tetrahedron Lett., 46, 2137-2140 (2005).
3. Werner B., Domling A., Molecules, 8, 53-66 (2003).
4. Domling A., Ugi I., Angew. Chem., Int. Ed., 39, 3169-3210 (2002).
5. Kappe C. O., Acc. Chem. Res., 33, 879-888 (2000).
6. Elinson M. N., Dorofeev A. S., Feducovich S. K., Gorbunov S. V., Nasybullin R. F., Stepanov N. O., Nikishin G. I., Tetrahedron Lett., 47, 7629-7633 (2006).
7. Sun W., Cama L. J., Birzin E. T., Warrier S., Locco L., Mosley R., Hammond M. L., Rohrer S. P., Bioorg. Med. Chem. Lett., 16, 1468-1472 (2006).
8. Stachulski A. V., Berry N. G., Lilian Low A. C., Moores S. L., Row E., Warhurst D. C., Adagu I. S., Rossignol J. F., J. Med. Chem., 49, 1450-1454 (2006).
9. Gesson J. P., Fonteneau N., Mondon M., Charbit S., Ficheux H., Schutze F., U. S. Patent 6,965,039 B2 (2005).
10. Lunt E., "Comprehensive Organic Chemistry," Vol.4, ed. by Barton D., Ollis W. D., Pergamon, Oxford, 1974, p. 493.
11. Brown J. D., "Comprehensive Heterocyclic Chemistry," Vol.3, ed. by Katrizky A. R., Rees C. W., Pergamon, Oxford, 1984, p. 57.
12. Sasaki T., Minamoto K., Suzuki T., Yamashita S., Tetrahedron, 36, 865-870 (1980), and references cited therein.
13. Bradshow T. K., Hutchinson D. W., Chem. Soc. Rev., 6, 43-62 (1977).
14. Marumoto R., Furukawa Y., Chem. Pharm. Bull., 25, 2974-2982 (1977).
15. Jones A. S., Sayers J. R., Walker R. T., De Clercq E., J. Med. Chem., 31, 268-271 (1988).
16. Griengl H., Wanek E., Schwarz W., Streicher W., Rosenwirth B., De Clercq E., J. Med. Chem., 30, 1199-1204 (1987).
17. Heidelberger, "Pyrimidine and Pyrimidine Antimetabolites in Cancer Medicine," ed. by Holland J. F., Frei E., Lea and Febiger, Philadelphia, 1984, p. 801.
18. Miyasaka T., Tanaka H., Baba M., Hayakawa H., Walker R. T., Balzarini J., De Qlercq E., J. Med. Chem., 32, 2507-2509 (1989).
19. Baba M., Tanaka H., De Clercq E., Pauwels R., Balzarini J., Schols D., Nakashima H., Perno C. F., Walker R. T., Miyasaka T., Biochem. Biophys. Res. Commun., 165, 1375-1381 (1989).
20. De Clercq E., Med. Res. Rev., 13, 229-258 (1993).
21. Fellahi Y., Dubois P., Agafonov V., Moussa F., Ombetta-Goka J. E., Guenzet J., Frangin Y., Bull. Soc. Chim. Fr., 133, 869-874 (1996).
22. Sharma P., Rane N., Gurram V. K., Bioorg. Med. Chem. Lett., 14, 4185-4190 (2004).
23. Elnagdi M. H., Elmoghayar M. R. H., Elgemeie G. F., Adv. Heterocycl. Chem., 41, 319-376 (1984).
24. Suzuki N., Chem. Pharm. Bull., 28, 761-768 (1980).
25. Prakash L., Shaihla M., Mital R. L., Pharmazie, 44, 490 (1989).
26. Heber D., Heers C., Ravens U., Pharmazie, 48, 537-542 (1993).
27. Yoneda F., Hirayama R., Yamashita M., Chem. Lett., 9, 1157-1160 (1980).
28. Yoneda F., Hirayama R., Yamashita M., J. Heterocycl. Chem., 19, 301-304 (1982).
29. Chen X., Tanaka K., Yoneda F., Chem. Pharm. Bull., 38, 307-311 (1990).
30. Liu Z., Li D., Li S., Bai D., He X., Hu, Y., Tetrahedron, 63, 1931- 1936 (2007).
31. Adib M., Sayahi M. H., Ziyadi H., Bijanzadeh H. R., Zhu L. G., Tetrahedron, 63, 11135-11140 (2007).
32. Cikotiene I., Kairys V., Buksnaitiene R., Morkunas M., Rudys S., Brukstus A., Fernandes M. X., Tetrahedron, 65, 5752-5759 (2009).
33. Nandi G. C., Samai S., Kumar R., Singh M. S., Tetrahedron, 65, 7129-7134 (2009).
34. Sasada T., Kobayashi F., Sakai N., Konakahara T., Org. Lett., 11, 2161-2164 (2009).
35. Devi I., Kumar B. S. D., Bhuyan P. J., Tetrahedron Lett., 44, 8307-8310 (2003).
36. Bazgir A., Seyyedhamzeh M., Yasaei Z., Mirzaei P., Tetrahedron Lett., 48, 8790-8794 (2007).
37. Sayyafi M., Seyyedhamzeh M., Khavasi H. R., Bazgir A., Tetrahedron, 64, 2375-2378 (2008).
38. Dabiri M., Delbari A. S., Bazgir A., Synlett, 2007, 821-823 (2007).
39. Dabiri M., Delbari A. S., Bazgir A., Heterocycles, 71, 543-548 (2007).
40. Bazgir A., Noroozi Tisseh Z., Mirzaei P., Terahedron Lett., 49, 5165-5168 (2008).
41. Ghahremanzadeh R., Imani Shakibaei G., Bazgir A., Synlett, 2008, 1129-1133 (2008).
42. Imani Shakibaei G., Khavasi H. R., Mirzaei P., Bazgir A., J. Heterocycl. Chem., 45, 1481-1484 (2008).
43. Ghahremanzadeh R., Azimi S. C., Gholami N., Bazgir A., Chem. Pharm. Bull., 56, 1617-1620 (2008).
44. Bazgir A., Mohammadi Khanaposhtani M., Abolhasani Soorki A., Bioorg. Med. Chem. Lett., 18, 5800-5803 (2008).
45. Dabiri M., Azimi S. C., Khavasi H. R., Bazgir A., Tetrahedron, 64, 7307-7311 (2008).
46. Dabiri M., Arvin-Nezhad H., Khavasi H. R., Bazgir A., J. Heterocycl. Chem., 44, 1009-1011 (2007).
47. Dabiri M., Azimi S. C., Arvin-Nezhad H., Bazgir A., Heterocycles, 75, 87-93 (2008)
48. Dabiri M., Arvin-Nezhad H., Khavasi H. R., Bazgir A., Tetrahedron, 63, 1770-1774 (2007).
49. Jadidi K., Ghahremanzadeh R., Bazgir A., J. Comb. Chem., 11, 341-344 (2009).
50. Ghahremanzadeh R., Sayyafi M., Ahadi S., Bazgir A., J. Comb. Chem., 11, 393-396 (2009).
51. Jadidi K., Ghahremanzadeh R., Bazgir A., Tetrahedron, 65, 2005- 2009 (2009).
52. Khoshkholgh M. J., Balalaie S., Gleiter R., Rominger F., Tetrahedron, 64, 10924-10929 (2008).
53. Deb M. L., Bhuyan P. J., Tetrahedron Lett., 46, 6453-6456 (2005).
54. Xu Y., Dolbier W. R. Jr., Tetrahedron, 54, 6319-6328 (1998).