Microwave-assisted N-nitroarylation of some pyrimidine and purine nucleobases

Canadian Journal of Chemistry

Volumn 84, Issue 7, 2006, Pages 979-985

  Khalafi Nezhad, Ali ^a   Zare, Abdolkarim ^a   Parhami, Abolfath ^a   Rad Soltani, Mohammad Navid ^b   Nejabat, Gholam Reza ^a  

^a SHIRAZ UNIVERSITY   (Iran)

^b SHIRAZ UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Microwave; N nitroarylation; Purine; Pyrimidine; SNAr

Indexed keywords

CESIUM COMPOUNDS; MICROWAVES; ORGANIC SOLVENTS; REACTION KINETICS; SILICA; SYNTHESIS (CHEMICAL);

N-NITROARYLATION; PURINE; PYRIMIDINE; SNAR;

NITROGEN COMPOUNDS;

NUCLEIC ACID BASE; PURINE NUCLEOBASE; PYRIMIDINE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MEDICAL RESEARCH; MICROWAVE RADIATION;

EID: 33751205922     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-119     Document Type: Article

References (70)

1. (a) M. Negwer and H.-G. Scharnow. Organic-chemical drugs and their synonyms. 8th ed. Wiley-VCH, Weinheim, Germany. 2001;
2. (b) G. Thomas. Medicinal chemisty. John Wiley and Sons Ltd., New York. 2000;
3. (c) A.R. Gennaro. Remington: the science and practice of pharmacy. 19th ed. Vol. 2. Mack Publishing Company, Easton, Penn. 1995;
4. (d) B.G. Katzung. Basic clinical pharmacology. 8th ed. McGraw-Hill, New York. 2001;
5. (e) A. Kleeman, J. Engel, B. Kutscher, and D. Reichert. Pharmaceutical substances. 3rd ed. Thieme, Stuttgart and New York. 1999;
6. (f) E. De Clercq. Advance in antiviral drug design. Vol. 1. Edited by N.G. Johnsson. Jai Press Inc., Greenwich, Conn. 1993;
7. (g) C. Heidelberger. Cancer medicine. Edited by J.F. Holland and E. Frei. Lea and Febiger, Philadelphia, Penn. 1973.
8. (a) G. Qu, S. Han, Z. Zhang, M. Geng, and F. Xue. Can. J. Chem. 84, 819 (2006);
9. (b) H. Gao and A.K. Mitra. Synthesis, 329 (2000);
10. (c) S. Guillarme, S. Legoupy, N. Bourgougnon, A.-M. Aubertin, and F. Huet. Tetrahedron, 59, 9635 (2003);
11. (d) S. Guillarme, S. Legoupy, A.-M. Aubertin, C. Olicard, N. Bourgougnon, and F. François Huet, Tetrahedron, 59, 2177 (2003);
12. (e) A.-I. Hernandez, J. Balzarini, A. Karlsson, M.-J. Camarasa, and M.-J. Perez-Perez. J. Med. Chem. 45, 4254 (2002);
13. (f) I.M. Buck, A. Eleuteri, and C.B. Reese. Tetrahedron, 50, 9195 (1994).
14. (a) C.K. Chu and D.C. Baker (Editors). Nucleosides and nucleotides as antitumor and antiviral agents. Plenum Press, New York. 1993;
15. (b) L. Naesens, J. Balzarini, and E. De Clercq. Rev. Med. Virol. 4, 147 (1994);
16. (c) M.R. Harnden, A. Parkin, M.J. Parratt, and R.M. Perkins. J. Med. Chem. 36, 1343 (1993);
17. (d) E. De Clercq, A. Holy, I. Rosenberg, T. Sakuma, J. Balzarini, and P.C. Maudgal. Nature, 323, 464 (1986).
18. (a) G. Gosselin, L. Griffe, J.-C. Meillon, and R. Storer. Tetrahedron, 62, 906 (2006);
19. (b) A.D. Borthwick and K. Biggadike. Tetrahedron, 48, 571 (1992);
20. (c) Y.H. Jin, P. Liu, J. Wang, U. Das, R. Baker, J. Huggins, and C.K. Chu. J. Org. Chem. 70, 394 (2005);
21. (d) Y.-Y. Yang, W.-D. Meng, and F.-L. Qing. Org. Lett. 4257 (2004);
22. (e) M.J. Comin, J.B. Rodriguez, P. Russ, and V.E. Marquez. Tetrahedron, 59, 295 (2003).
23. (a) M. Yokoyama and A. Momotake. Synthesis, 1541 (1999);
24. (b) M. Koszytkowska-Stawinska and W. Sas. Tetrahedron Lett. 45, 5437 (2004).
25. (a) M. Yokoyama. Synthesis, 1637 (2000);
26. (b) N.A. Van Draanen, G.A. Freeman, S.A. Short, R. Harvey, R. Jansen, and G.W. Szczech. J. Med. Chem. 39, 538 (1996).
27. (a) R.D. Thompson, S. Secunda, J.W. Daly, and R.A. Olsson. J. Med. Chem. 34, 2877 (1991);
28. (b) H. Harada, O. Asano, T. Kawara, T. Inoue, T. Horizoe, N. Yasuda, K. Nagata, M. Murakami, J. Nagaoka, S. Kobayashi, I. Tanaka, and S. Abe. Bioorg. Med. Chem. 9, 2709 (2001).
29. R.J. Chorvat, R. Bakthavatchalam, J.P. Beck, P.J. Gilligan, R.G. Wilde, A.J. Cocuzza, F.W. Hobbs, R.S. Cheeseman, M. Curry, J.P. Rescinito, P. Krenitsky, D. Chidester, J.A. Yarem, J.D. Klaczkiewicz, C.H. Fernandez, R. Zaczek, L.W. Fitzgerald, S.-M. Huang, H.L. Shen, Y.N. Wong, B.M. Chien, C.Y. Quon, and A. Arvanitis. J. Med. Chem. 42, 833 (1999).
30. (a) R.K. Robine and G.R. Revankar. J. Heterocycl. Chem. 22, 601 (1985);
31. (b) C. Silipo and C. Hansch. J. Med. Chem. 19, 62 (1976);
32. (c) I. Moriguchi and Y. Kanada. Chem. Pharm. Bull. 25, 926 (1977).
33. M. Brakta, D. Murthy, L. Ellis, and S. Phadtare. Bioorg. Med. Chem. Lett. 12, 1489 (2002).
34. (a) B.R. Baker and W.F. Wood. J. Med. Chem. 12, 216 (1969);
35. (b) B.R. Baker and H.U. Siebeneick. J. Med. Chem. 14, 802 (1971).
36. (a) H.C. Koppel and R.K. Robins. J. Am. Chem. Soc. 80, 2751 (1958);
37. (b) H.C. Koppel, D.E. O'Brien, and R.K. Robins. J. Am. Chem. Soc. 81, 3046 (1959).
38. (a) D. Sen, A. Dasgupta, and P. Sengupta. Indian J. Chem. Sect. B: Org. Chem. 24, 952 (1985);
39. (b) W.M. Basyouni, H.M. Hosni, and S.M. Helmy. Egypt. J. Chem. 42, 587 (1999).
40. K.A.M. El-Bayouki, B. Haggag, and W.M. Basyouni. Egypt. J. Chem. 33, 243 (1990).
41. (a) B.R. Baker, W.F. Wood, and J.A. Kozma. J. Med. Chem. 11, 661 (1968);
42. (b) I. Chu and B.M. Lynch. J. Med. Chem. 18, 161 (1975);
43. (c) C.C. Cheng and R.K. Robins. J. Org. Chem. 21, 1240 (1956);
44. (d) S.M. Greenberg, L.O. Ross, and R.K. Robins. J. Org. Chem. 24, 1314 (1959);
45. (e) C.C. Cheng and R.K. Robins. J. Org. Chem. 23, 852 (1958);
46. (f) J.P. Beck, A.G. Arvanitis, M.A. Curry, J.T. Rescinito, L.W. Fitzgerald, P.J. Gilligan, R. Zaczek, and G.L. Trainor. Bioorg. Med. Chem. Lett. 9, 967 (1999);
47. (g) T. Kumagai, T. Okubo, H. Kataoka-Okubo, S. Chaki, S. Okuyama, and A. Nakazato. Bioorg. Med. Chem. 9, 1357 (2001).
48. (a) S. Ding, N.S. Gray, Q. Ding, and P.G. Schultz. Tetrahedron Lett. 42, 8751 (2001);
49. (b) A.K. Bakkestuen and L.-L. Gundersen. Tetrahedron Lett. 44, 3359 (2003);
50. (c) M. Tokumi, F. Keiichi, and F. Mitsutoshi. J. Chem. Soc. Perkin Trans. 1, 733 (1995);
51. (d) Y. Yue, Z.-G. Zheng, B. Wu, C.-Q. Xia, and X.-Q. Yu. Eur. J. Org. Chem. 5154 (2005);
52. (e) T. Zhou, T.-C. Li, and Z.-C. Chen. Helv. Chim. Acta, 88, 290 (2005).
53. (a) A. Loupy. Microwave in organic synthesis. Wiley-VCH, Weinheim, Germany. 2004;
54. (b) R.S. Varma. Advances in green chemistry: chemical synthesis using microwave irradiation. Astra Zeneca Research Foundation, Kavitha Printers, Bangalore, India. 2002;
55. (c) H.M. Kingston and S.J. Haswell. Microwave-enhanced chemistry. Fundamentals, sample preparation, and applications. American Chemical Society, Washington, D.C. 1997;
56. (d) J. Yin, X. Li, X. Wu, B. Chen, Z. Liu, and Q. Song. Can. J. Chem. 83, 2140 (2005);
57. (e) B.P. Joshi, A. Sharma, and A.K. Sinha. Can. J. Chem. 83, 1826 (2005).
58. (a) A. Khalafi-Nezhad, A. Zarea, M.N. Soltani Rad, B. Mokhtari, and A. Parhami. Synthesis, 419 (2005);
59. (b) A. Khalafi-Nezhad, M.N. Soltani Rad, and A. Khoshnood. Synthesis, 583 (2004);
60. (c) A. Khalafi-Nezhad, M.N. Soltani Rad, G.H. Hakimelahi, and B. Mokhtari. Tetrahedron, 58, 10341 (2002);
61. (d) A. Khalafi-Nezhad and B. Mokhtari. Tetrahedron Lett. 45, 6737 (2004).
62. (a) D. Singh, M.J. Wani, and A. Kumar. J. Org. Chem. 64, 4665 (1999);
63. (b) L.W. Dudycz and G.E. Wright. Nucleosides Nucleotides, 33 (1984);
64. (c) G.E. Wright and L.W. Dudycz, J. Med. Chem. 27, 175 (1984);
65. (d) K.C. Schneider and S.A. Benner. Tetrahedron Lett. 31, 335 (1990);
66. (e) M.-T. Chenon, R.J. Pugmire, D.M. Grant, R.P. Panzica, and L.B. Townsend. J. Am. Chem. Soc. 97, 4628 (1975);
67. (f) M.T. Crimmins, B.W. King, W.J. Zuercher, and A.L. Choy. J. Org. Chem. 65, 8499 (2000);
68. (g) J. Kjellberg and N.G. Johansson. Tetrahedron, 42, 6541 (1986);
69. (h) P. Gamer and S. Ramakanth. J. Org. Chem. 53, 1294 (1988).
70. A.I. Vogel. Textbook of practical organic chemistry. 4th ed. Longman Inc., London and New York. 1978.