The cohalogenation of 1-N-vinylpyrimidinediones: A new approach to nucleoside analogs

European Journal of Organic Chemistry

Volumn , Issue 8, 2000, Pages 1507-1516

  Baret, Nathalie ^a   Dulcere, Jean Pierre ^a   Rodriguez, Jean ^a   Pons, Jean Marc ^a   Faure, Robert ^b  

^a AIX MARSEILLE UNIVERSITY   (France)

^b Laboratoire MADIREL   (France)

Author keywords

CH interaction; Hydrogen transfer; Nucleoside analogs; Nucleosides; Radical reactions

Indexed keywords

NUCLEOSIDE ANALOG; PYRIMIDINE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; HALOGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034017718     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200004)2000:8<1507::AID-EJOC1507>3.0.CO;2-K     Document Type: Article

References (68)

1. [1a] D. A. Huryn, M. Okabe, Chem. Rev. 1992, 92, 1745-1768.
2. [1b] C. Périgaud, G. Gosselin, J. L. Imbach, Nucleosides, Nucleotides 1992, 11, 903-945.
3. [1c] E. De Clercq, in Design of Anti AIDS Drugs (Ed.: E. De Clercq), Pharmacochemistry Library, Vol. 14, Elsevier, Amsterdam, 1990.
4. L. J. Wilson, M. W. Hager, Y. A. El-Kattan, D. C. Liotta, Synthesis 1995, 1465-1479.
5. H. Mitsuya, S. Broder, Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 1911-1915.
6. [4a] A. De Mesmaeker, A. Walner, J. Lebreton, P. Hoffmann, V. Fritsch, R. M. Wolf, S. M. Freier, Angew. Chem. Int. Ed. Engl. 1994, 33, 226-229.
7. [4b] A. Walner, A. De Mesmaeker, Synlett 1995, 108-110.
8. [4c] J. Fiandor, S. Y. Tam, Tetrahedron Lett. 1990, 31, 597-600.
9. [5a] J.-F. Lavallée, G. Just, Tetrahedron Lett. 1991, 32, 3469-3472.
10. [5b] M. E. Jung, J. M. Gardiner, J. Org. Chem. 1991, 56, 2614-2615.
11. [5c] M. E. Jung, C. Castro, J. M. Gardiner, Tetrahedron Lett. 1991, 32, 5717-5720.
12. [5d] R. D. Walkup, M. D. Mosher, Tetrahedron Lett. 1994, 35, 8545-8548.
13. [5e] U. Niedballa, H. Vorbrüggen, J. Org. Chem. 1974, 39, 3654-3660, 3660-3663, 3663-3667, 3668-3671, 3672-3674.
14. [5f] H. Vorbrüggen, K. Krolikiewicz, B. Bennua, Chem. Ber. 1981, 114, 1234-1255.
15. [5g] H. Vorbrüggen, G. Hofle, Chem. Ber. 1981, 114, 1256-1268.
16. [5h] B. H. Lipshutz, H. Hayakawa, K. Kato, R. F. Lowe, K. L. Stevens, Synthesis 1994, 1476-1484.
17. [6a] H.-J. Gi, Y. Xiang, R. F. Schinazi, K. Zhao, J. Org. Chem. 1997, 62, 88-92.
18. [6b] Y. Xiang, J. Chen, R. F. Schinazi, K. Zhao, Bioorg. Med. Chem. Lett. 1996, 6, 1051-1054.
19. [6c] D. R. Adams, A. S. F. Boyd, R. Ferguson, D. S. Grierson, C. Monneret, Nucleosides, Nucleotides 1998, 17, 1053-1075.
20. A. Leggio, A. Liguori, A. Procopio, C. Siciliano, G. Sindona, Tetrahedron Lett. 1996, 37, 1277-1280.
21. J.-P. Dulcère, N. Baret, J. Rodriguez, Synlett 1995, 923-924.
22. M. Sharma, M. Bobek, Tetrahedron Lett. 1990, 31, 5839-5842.
23. [10a] J. Wengel, R. F. Shinazi, M. H. Caruthers, Bioorg. Med. Chem. 1995, 3, 1223-1229.
24. [10b] A. Matsuda, H. Okajima, T. Ueda, Heterocycles 1989, 29, 25-28.
25. [11a] C. Scheuer-Larsen, H. M. Pfundheller, J. Wengel, J. Org. Chem. 1995, 60, 7298-7303.
26. [11b] S. Czernecki, A. Ezzitouni, P. Krausz, Synthesis 1990, 651-653.
27. [11c] S. Czernecki, A. Ezzitouni, J. Org. Chem. 1992, 57, 7325-7328.
28. J. Rodriguez, J.-P. Dulcère, Synthesis 1993, 1177-1205.
29. [13a] A. L. Campbell, G. R. Lenz, Synthesis 1987, 421-452.
30. [13b] M. Natsume, M. Wada, Chem. Pharm. Bull. (Tokyo) 1975, 23, 2567-2572; 1976, 24, 2651-2656, 2657-2660.
31. [13b] M. Natsume, M. Wada, Chem. Pharm. Bull. (Tokyo) 1975, 23, 2567-2572; 1976, 24, 2651-2656, 2657-2660.
32. J. E. Baldwin J. Chem. Soc., Chem. Commun. 1976, 734-736.
33. [15a] K. L. Carraway, P. C. Huang, T. G. Scott, in Synthetic Procedures in Nucleic Acid Chemistry, J. Wiley Sons, New York, 1969, Vol. 1, pp. 3-5.
34. [15b] D. T. Browne, in Synthetic Procedures in Nucleic Acid Chemistry, J. Wiley Sons, New York, 1969, Vol. 1, pp. 96-97.
35. [15c] N. J. Leonard, T. G Scott, P. C. Huang, J. Am. Chem. Soc. 1967, 89, 7137-7138.
36. [16a] J. Pitha, P. O. P. Ts'O, J. Org. Chem 1968, 33, 1341-1344.
37. [16b] N. Ueda, K. Kondo, M. Kono, K. Takemoto, M. Imoto, Makromol. Chem. 1968, 120, 13-20.
38. [16c] J. Zhou, P. B. Shevlin, Synth. Commun. 1997, 27, 3591-3597.
39. [16d] A simple preparation of N-vinyl derivatives of nucleic acid bases - not including uracil - has recently been reported: A. Ciapetti, M. Taddei, Tetrahedron 1998, 54, 11305-11310.
40. [17a] P. F. Keusenkothen, M. B. Smith, J. Chem. Soc., Perkin Trans. 1 1994, 2485-2492.
41. [17b] C. A. Zezza, M. B. Smith, J. Org. Chem. 1988, 53, 1161-1167.
42. E. Bayer, K. Geckeler, Angew. Chem. Int. Ed. Engl. 1979, 18, 533-534.
43. K. A. Cruickshank, J. Jiricny, C. B. Reese, Tetrahedron Lett. 1984, 25, 681-684.
44. T. Gharbaoui, R. Benhida, J. Chastanet, A. Lechevallier, P. Maillos, R. Beugelmans, Bull. Soc. Chim. Fr. 1994, 131, 561-574.
45. [21a] O. F. Schall, G. W. Gokel, J. Am. Chem. Soc. 1994, 116, 6089-6100.
46. [21b] J. S. Nowick, J. S. Chen, G. Noronha, J. Am. Chem. Soc. 1993, 115, 7636-7644.
47. J.-P. Dulcère, N. Baret, J. Rodriguez, R. Faure, Synlett 1995, 705-706.
48. [23a] J. S. Yadav, M. C. Chander, B. V. Joshi, Tetrahedron Lett. 1988, 29, 2737-2740.
49. [23b] S. Takano, K. Samizu, T. Sugihara, K. Ogasawara, J. Chem. Soc., Chem. Commun. 1989, 1344-1345.
50. [23c] M. Lopp, T. Kanger, A. C. Müraus, T. Pehk, U. Lille, Tetrahedron: Asymmetry 1991, 2, 943-944.
51. [23d] E. C. Taylor, R. Dötzer, J. Org. Chem. 1991, 56, 1816-1822.
52. [23e] J. P. Vigneron, R. Méric, M. Larchevèque, A. Debal, J. Y. Lallemand, Tetrahedron 1984, 40, 3521-3529.
53. [23f] O. Yamada, K. Ogasawara, Synlett 1995, 427-428.
54. [24a] M. Okabe, M. Abe, M. Tada, J. Org. Chem. 1982, 47, 1775-1777.
55. [24b] B. Giese, Radicals in Organic Synthesis, Pergamon Press, New York, 1986, and references cited therein.
56. R. E. Hurd, J. Magn. Reson. 1990, 87, 422-428.
57. R. E. Hurd, B. K. John, J. Magn. Reson. 1991, 91, 648-653.
58. W. Wilker, D. Leibfritz, R. Kerssebaum, W. Bermel, Magn. Reson. Chem. 1993, 31, 287-292.
59. G. Bodenhausen, H. Kogler, R. R. Ernst, J. Magn. Reson. 1984, 55, 370-388.
60. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
61. [30a] M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665-8701.
62. [30b] D. Stien, D. Crich, M. P. Bertrand, Tetrahedron 1998, 54, 10779-10788.
63. G. B. Jones, B. Chapman, Synthesis 1995, 475-497.
64. D. L. J. Clive, Y. Tao, A. Khodabocus, Y-J. Wu, A. G. Angoh, S. M. Bennett, C. N. Boddy, L. Bordeleau, D. Kellner, G. Kleiner, D. S. Middleton, C. J. Nichols, S. R. Richardson, P. G. Vernon, J. Am. Chem. Soc. 1994, 116, 11275-11286.
65. G. A. Molander, L. S. Harring, J. Org. Chem. 1990, 55, 6171-6176.
66. [34a] J. C. Litten, C. Epple, C. J. Leumann, Bioorg. Med. Chem. Lett. 1995, 5, 1231-1234.
67. [34b] I. Bousquié, V. Madiot, J.-C. Florent, C. Monneret, Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
68. [34c] K. Hisa, A. Kittaka, H. Tanaka, K. Yamaguchi, T. Miyasaka, Nucleosides, Nucleotides 1996, 15, 85-96.