Microwave-assisted Michael addition of some pyrimidine and purine nucleobases with α,β-unsaturated esters: A rapid entry into carboacyclic nucleoside synthesis

Synthesis

Volumn , Issue 3, 2005, Pages 419-424

  Khalafi Nezhad, A ^a   Zarea, A ^a   Soltani Rad, M N ^a   Mokhtari, B ^a   Parhami, A ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

, unsaturated esters; Carboacyclic nucleosides; Michael addition; Microwave; Nucleobases

Indexed keywords

ADDITION REACTIONS; ALKYLATION; ESTERS; NITROGEN COMPOUNDS; REACTION KINETICS;

MICHAEL ADDITION; NUCLEOBASES; REGIOSELECTIVITY; TETRABUTYLAMMONIUM BROMIDE (TBAB);

SYNTHESIS (CHEMICAL);

1,4 DIAZABICYCLO[2.2.2]OCTANE; 3 (2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)PROPIONIC ACID ETHYL ESTER; 3 (6 AMINOPURIN 9 YL)PROPIONIC ACID ETHYL ESTER; ESTER DERIVATIVE; NUCLEIC ACID BASE; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; DISSOCIATION; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; MICROWAVE RADIATION; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 14644435161     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834950     Document Type: Article

References (59)

1. (a) Langa, F.; de la Cruz, P.; de la Hoz, A.; Diaz-Ortiz, A.; Diez-Barra, E. Contemp. Org. Synth. 1997, 65, 373.
2. (b) Vega, J. A.; Cueto, S.; Ramos, A.; Vaquero, J. J.; Garcia-Navio, J. L.; Alvarez-Builla, J.; Ezquerra, J. Tetrahedron Lett. 1996, 37, 6413.
3. (c) Almena, I.; Diaz-Ortiz, A.; Diez-Barra, E.; de la Hoz, A.; Loupy, A. Chem. Lett. 1996, 37, 333.
4. (d) Carrillo-Munoz, J. R.; Bouvet, D.; Guibe-Jampel, E.; Loupy, A.; Petit, A. J. Org. Chem. 1996, 61, 7746.
5. (e) Herradon, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455.
6. (f) Forfar, I.; Cabil do, P.; Claramunt, R. M.; Elguero, J. Chem. Lett. 1994, 2079.
7. (a) Khalafi-Nezhad, A.; Soltani Rad, M. N.; Hakimelahi, G. H. Helv. Chim. Acta 2003, 86, 2396.
8. (b) Khalafi-Nezhad, A.; Alamdari, F.; Zekri, N. Tetrahedron 2000, 56, 7503.
9. (c) Khalafi-Nezhad, A.; Hashemi, A. Iran. J. Chem. Chem. Eng. 2001, 20, 9; Chem. Abstr. 2002, 137, 232608.
10. (c) Khalafi-Nezhad, A.; Hashemi, A. Iran. J. Chem. Chem. Eng. 2001, 20, 9; Chem. Abstr. 2002, 137, 232608.
11. (d) Khalafi-Nezhad, A.; Mokhtari, B.; Soltani Rad, M. N. Tetrahedron Lett. 2003, 44, 7325.
12. (e) Khalafi-Nezhad, A.; Hashemi, A. J. Chem. Res., Synop. 1999, 720.
13. (f) Khalafi-Nezhad, A.; Soltani Rad, M. N.; Khoshnood, A. Synthesis 2004, 583.
14. (a) Microwave in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2002.
15. (b) Varma, R. S. Advances in Green Chemistry: Chemical Synthesis Using Microwave Irradiation; Astra Zeneca Research Foundation, Kavitha Printers: Bangalore, India, 2002.
16. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95.
17. (d) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
18. (e) Kuhnert, N. Angew. Chem. Int. Ed. 2002, 41, 1863.
19. (f) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
20. (g) Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Mathews, NC, 2002.
21. (h) Ahluwalia, V. K.; Aggarwal, R. Organic Synthesis: Special Techniques, Chap. 3; Alpha Science International Ltd.: Pangbourne, U.K., 2001, 90-114.
22. (i) Microwave-Enhanced Chemistry. Fundamentals, Sample Preparation, and Applications; Kingston, H. M.; Haswell, S. J., Eds.; American Chemical Society: Washington, D.C., 1997.
23. (j) Wathey, B.; Tierney, J.; Lidstrom, P.; Westman, J. Drug Discov. Today 2002, 7, 373.
24. (k) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
25. (l) Varma, R. S. Green Chem. 1999, 1, 43.
26. (m) Caddick, S. Tetrahedron 1995, 51, 10403.
27. (a) Lira, E. P.; Huffman, C. W. J. Org. Chem. 1966, 31, 2188.
28. (b) Prevost, N.; Rouessac, F. Tetrahedron Lett. 1997, 38, 4215.
29. (c) Cai, Y.; Sun, X.-F.; Wang, N.; Lin, X.-F. Synthesis 2004, 671.
30. (d) Lazrek, H. B.; Rochdi, A.; Khaider, H.; Barascut, J.-L.; Imbach, J.-L.; Balzarini, J.; Witvrouw, M.; Pannecouque, C.; De Clercq, E. Tetrahedron 1998, 54, 3807.
31. (e) Lazrek, H. B.; Khaider, H.; Rochdi, A.; Barascut, J.-L.; Imbach, J.-L. Tetrahedron Lett. 1996, 37, 4701.
32. (f) Geen, G. R.; Kincey, P. M. Tetrahedron Lett. 1992, 33, 4609.
33. (g) Hamden, M. R.; Parkin, A.; Paratt, M. J.; Perkins, R. M. J. Med. Chem. 1993, 36, 1343.
34. (h) Lazrek, H. B.; Khaider, H.; Rochdi, A.; Barascut, J.-L.; Imbach, J.-L. Nucleosides Nucleotides 1994, 13, 811.
35. (i) Baker, B. R.; Tanna, P. M. J. Org. Chem. 1965, 30, 2857.
36. (j) Scheiner, P.; Geer, A.; Bucknor, A. M.; Gadler, H.; Price, R. W. Nucleosides Nucleotides 1989, 32, 73.
37. (a) De Clercq, E.; Sakuma, T.; Baba, M.; Pauwels, R.; Balzarini, J.; Rosenberg, I.; Holy, A. Antiviral Res. 1987, 8, 261.
38. (b) Naesens, L.; Balzarini, J.; De Clercq, E. Rev. Med. Virol. 1994, 4, 147.
39. (c) De Clercq, E.; Holy, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. Nature 1986, 323, 464.
40. (d) Neyts, J.; De Clercq, E. Biochem. Pharmacol. 1994, 47, 39.
41. (e) De Clercq, E. Medical Virology 1995, 5, 149.
42. (f) De Clercq, E. Biochem. Pharmacol. 1991, 42, 963.
43. Doerge, R. F. Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 8th Ed.; J. B. L. Lippincott Company: Philadelphia, 1982, 295-334.
44. Buchi, G.; Rosenthal, D. J. Am. Chem. Soc. 1956, 78, 3860.
45. (a) Hayashi, Y.; Nishimura, K. Chem. Lett. 2002, 3, 296.
46. (b) Ranu, B. C.; Dey, S. S.; Hajra, A. Tetrahedron 2003, 59, 2417.
47. (c) Soriente, A.; Spinella, A.; De Rosa, M.; Giordano, M.; Scettri, A. Tetrahedron Lett. 1997, 38, 289.
48. (d) Ranu, B. C.; Saha, M.; Bhar, S. Synth. Commun. 1997, 27, 621.
49. (a) Shaikh, N. S.; Deshpande, V. H.; Bedekar, A. V. Tetrahedron 2001, 57, 9045.
50. (b) Laszlo, P.; Montaufier, M.T.; Randriamahefa, S. L. Tetrahedron Lett. 1990, 31, 4867.
51. (c) Christoffers, J. Synlett 2001, 723.
52. (d) Nelson, J. H.; Howells, P. N.; DeLullo, G. C.; Landen, G. L.; Henry, R. A. J. Org. Chem. 1980, 45, 1246.
53. (e) Meseguer, M.; Moreno-Manas, M.; Vallribera, A. Tetrahedron Lett. 2000, 41, 4093.
54. (f) Christoffers, J. J. Chem. Soc., Perkin Trans. 1 1997, 3141.
55. (g) van Westrenen, J.; Roggen, R. M.; Hoefnagel, M. A.; Peters, J. A.; Kieboom, A. P. G.; van Beklum, H. Tetrahedron 1990, 46, 5741.
56. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
57. (i) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 11204.
58. For monographies on ionic liquids, see: Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, 2002.
59. Vogel, A. I. Practical Organic Chemistry; Longman, Green and Co.: London, 1954, 161-176.