An eco-friendly catalytic route for synthesis of 4-amino-pyrazolo[3,4-d]pyrimidine derivatives by Keggin heteropolyacids under classical heating and microwave irradiation

Journal of Molecular Catalysis A: Chemical

Volumn 256, Issue 1-2, 2006, Pages 238-241

  Heravi, Majid M ^a   Rajabzadeh, Ghadir ^b   Bamoharram, Fatemeh F ^c   Seifi, Nasim ^c  

^a ALZAHRA UNIVERSITY   (Iran)

^b Khorasan Science & Technology Park   (Iran)

^c ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

4 Amino pyrazolo 3,4 d pyrimidine; Heteropolyacid; Keggin; Microwave irradiation; Silica supported sulfuric acid; Solid acid

Indexed keywords

CATALYST ACTIVITY; IRRADIATION; MICROWAVES; SULFURIC ACID; SYNTHESIS (CHEMICAL);

4-AMINO-PYRAZOLO[3,4-D]PYRIMIDINE; HETEROPOLYACID; MICROWAVE IRRADIATION; SILICA SUPPORTED SULFURIC ACID; SOLID ACIDS;

NITROGEN COMPOUNDS;

EID: 33747584626     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.04.016     Document Type: Article

References (60)

1. Gadd R.E.A., and Henderson J.F. Can. J. Biochem. 48 (1970) 295
2. Krenitzky T.A., NeiL S.M., Elion G.B., and Hitchings G.H. J. Biol. Chem. 244 (1969) 4779
3. Iwamoto K., and Martin W. J. Biochem. Pharm. 23 (1974) 3199 and references cited there in
4. Ownes M.J. Pharm. Rev. 43 (1991) 425
5. C.Y. Liang (Pfizer inc.) PCTInt. APPL. WO 94 13, 677 (CI.Co7D487/04), 23 June 1994, US Appl. 992, 229, 17 December 1992, 62 pp.
6. C.L. River, J.E.F. Rivier, W.W. Vale, Jr., all of La Jolla; M.R. Brown, Del Mar, al of California, US patent number 4,605,642. Date of patent: August 12, 1986.
7. M.E. Abreu, Baltimore; W. Rzeszotarski, Millersville; D.J. Kyle, Baltimore; R.N. Hiner, Baltimore; R.N. Hiner, Baltimore; R.L. Elliott, Baltimore, all of Md. US patent number 5,063,245. Date of patent: November 5, 1991.
8. Minami T., Nakagawa H., Nabeshima H., Kadota M., Namikawa E., Kawaki K., and Okazaki H.Y. J. Biol. Pharm. Bull. 17 (1994) 1032
9. Minami T., Nakagawa H., Ichii M., Kadota E., and Okazaki Y. J. Biol. Pharm. Bull. 17 (1994) 201
10. Skipper H.E., Robins R.K., and Thomson J.R. Proc. Soc. Exp. Biol. Med. 89 (1995) 594
11. HSU T.C., Robins R.K., and Cheng C.C. Science 123 (1956) 848
12. Skipper H.E., Robins R.K., Thomson J.R., Brockman C.C., and Schabel R.W. J. Cancer Res. 17 (1957) 579
13. Lynch B.M., Robins R.K., and Change C.C. J. Chem. Soc. (1958) 2973
14. Hendson M.C., Grennne S.J., Reggio B.C., Shi W., and Swan K.F. Endocrinology 138 (1994) 1385
15. Davidson K.G., and Acton S.M. Am. J. Physiol. 272 (1997) Liob-L 114
16. Cheng C.C., and Robins R.K. J. Org. Chem. 21 (1956) 1240
17. Heravi M.M., Tajbakhsh M., Rahimzadeh M., Davoodnia A., and Aghapoor K. Synth. Commun. 29 (1999) 4417
18. Heravi M.M., Aghapoor K., and Nooshabadi M.A. Synth. Commun. 28 (1998) 233
19. Heravi M.M., Montazeri N., Rahimizadeh M., Bakavoli M., Ghassemzadeh M., and Ghassemzadeh M. Monatsh 132 (2001) 1225
20. Heravi M.M., Montazeri N., Rahimzadeh M., Bakavoli M., and Ghassemzadeh M. J. Chem. Res. 10 (2000) 464
21. OKuhara T., Mizuno N., and Misono M. Adv. Catal. 41 (1996) 113
22. Mizuno N., and Misono M. J. Mol. Catal. 86 (1994) 319
23. Izumi Y., Urabe K., and Onaka M. Zeolite, Clay and Heretopoly Acid in Organic Reactions (1992), Kadansha, Tokyo
24. Kozhevinkov I.V. Chem. Rev. 98 (1998) 171
25. Ono Y. In: Thomas J.M., and Zamaraev (Eds). Perspectives in Catalysis (1992), Blackwell, London 431
26. Kozhevinkov I.V. Catalysis for Fine Chemicals. Catalysis by Poly Oxometalates vol. 2 (2002), Wiley, Chichester
27. Misono M., and Nojiri N. Appl. Catal. 64 (1990) 1
28. Time feeva M.N. Appl. Catal. 256 (2003) 19
29. Kozhevinkov I.V. Catal. Rev. Sci. Eng. 37 (1995)
30. For a recent review in the area see:. Kappe C.O. Angew. Chem. Int. Ed. 43 (2004) 6250-6284
31. For the most cited book on microwave in chemistry see:. In: Loupy A. (Ed). Microwaves in Organic Synthesis (2002), Wiley-VCH Verlay Gmbh&Co KGaA, Weinhein
32. For CEM corp: Milestone srl.
33. Favretto L. Mol. Divers. 7 (2003) 287-291 detailed description of single-mode microwave reactors with integrate robotics were recently published
34. Heravi M.M., Ajami D., Mojtahedi M.M., and Ghassemzadeh M. Tetrahedron Lett. 40 (1999) 561
35. Heravi M.M., Ajami D., and Ghassemzadeh M. Synthesis 3 (1999) 39
36. Heravi M.M., Ajami D., Aghapoor K., and Ghassemzadeh M. Chem. Commun. (1999) 833
37. M.M. Heravi, H.A. Oskooie, S. Yazdanpanah, M. M. Mojtahedi (2004) 212.
38. Heravi M.M., Hydarzadeh F., Farhangi Y., and Ghassemzadeh M. J. Chem. Res. 2 (2004) 137
39. Heravi M.M., and Bakavoli M. J. Chem. Res. 1 (1995) 480
40. Heravi M.M., Rajabzadeh G.H., Rahimzadeh M., Bakavoli M., and Ghassemzadeh M. Phosphorus Sulfur Silicon 161 (2000) 7
41. Heravi M.M., Beheshtiha Y.Sh., Nami N., and Hekmatshoar R. Phosphorus Sulfur Silicon 165 (2000) 285
42. Heravi M.M., Montazeri N., Ra himzadeh M., Bakavoli M., and Ghassemzadeh M. J. Heterocylic. Chem. 42 (2005) 1021
43. Heravi M.M., Kivanloo A., Rahimzadeh M., Bakavoli M., and Ghassemzaeh M. Tetrahedron Lett. 45 (2004) 5747
44. Heravi M.M., Kivanloo A., Rahimzadeh M., Bakavoli M., and Ghassemzadeh M. Tetrahedron Lett. 46 (2005) 1607
45. Heravi M.M., Beheshtiha Y.Sh., Nami N., and Ghassemzadeh M. Phosphorus Sulfur Silicon 174 (2001) 129
46. Alizadeh M.H., Razavi H., Bamoharram F.F., and Hassanzadeh M.H. Kinet. Catal. 44 (2003) 524
47. Bamoharram F.F., Roshani M., and Alizadeh M.H. J. Braz. Chem. Soc. 17 (2006) 505
48. Bamoharram F.F., Heravi M.M., Roshani M., Gahangir M., and Gharib A. Appl. Catal. 302 (2006) 42
49. F.F. Bamoharram, M.M. Heravi, M. Roshani, M. Jahangir, A. Gharib, Appl. Catal. (2006), submitted for publication.
50. Bamoharram F.F., Heravi M.M., Roshani M., Gharib A., and Gahangir M. J. Mol. Catal. 252 (2006) 90
51. M.M. Heravi, F. Derikvand, F.F. Bamoharram, 242 (2005) 173.
52. Heravi M.M., Motamedi R., Seifi N., and Bamoharram F.F. J. Mol. Catal. 249 (2006) 1
53. Heravi M.M., Bakhtiari Kh., and Bamoharram F.F. Cat. Commun. 7 (2006) 373
54. M.M. Heravi, Kh. Bakhtiari, F.F. Bamoharram, Cat. Commun. (2006) in press.
55. Hino T., Anzai T., and Kuramoto N. Tetrahedron Lett. 47 9 (2006, February 27) 1429-1432 and the references cited therein
56. Hu C., Hashimoto M., Okuhara T., and Misono M. J. Catal. 143 (1993) 437
57. Kozhevnikov I.V. Russ. Chem. Rev. (English translation) 56 (1987) 811
58. Kozhevnikov I.V., Kloetstra K.R., Sinnema A., Zandbergen H.W., and Van Bekkum H. J. Mol. Catal. 114 (1996) 287
59. Jeffery B., Nancy Eudy H., Morton F.M., George siegel O., and Marshal M. J. Am. Chem. Soc. 104 14 (1982) 1403-1404
60. Heravi M.M., Ajami D., and Ghassemzadeh M. Synth. Commun. (1999) 1013