Addition of nucleophiles to 6-vinylpurines

Acta Chemica Scandinavica

Volumn 51, Issue 11, 1997, Pages 1116-1124

  Øverås, Anniken T ^a   Bakkestuen, Anne Kristin ^a,b   Gundersen, Lise Lotte ^a   Rise, Frode ^a  

^a UNIVERSITY OF OSLO   (Norway)

^b Weiders Farmasøytiske A S   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000462388     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.51-1116     Document Type: Article

References (36)

1. See for instance: (a) Montgomery, J. A. and Hewson, K. J. Med. Chem. 11 (1968) 49; (b) Abiru, T., Yamaguchi, T., Watanabe, Y., Kogi, K., Aihara, K. and Matsuda, A. Eur. J. Pharmacol. 196 (1991) 69; (c) Matsuda, A., Shinozaki, M., Yamaguchi, T., Homma, H., Nomoto, R., Miyasaka, T., Watanabe, Y. and Abiru, T. J. Med. Chem. 35 (1992) 241; (d) Jacobson, K. A., Shi, D., Gallo-Rodrigues, C., Manning, M., Jr., Müller, C., Daly, J. W., Neumeyer, J. L., Kiriasis, L. and Pfleiderer, W. J. Med. Chem. 36 (1993) 2639 and references therein; (e) Sági, G., Ötvös, L., Ikeda, S., Andrei, G., Snoeck, R. and De Clercq, E. J. Med. Chem. 37 (1994) 1307; (f) Estep, K. G., Josef, K. A., Bacon, E. R., Carabateas, P. M., Rumney, S., IV., Pilling, G. M., Krafte, D. S., Volberg, W. A., Dillon, K., Dugrenier, N., Briggs, G. M., Canniff, P. C., Gorczyca, W. P., Stankus, G. P. and Ezrin, A. M. J. Med. Chem. 38 (1995) 2582.
2. See for instance: (a) Montgomery, J. A. and Hewson, K. J. Med. Chem. 11 (1968) 49; (b) Abiru, T., Yamaguchi, T., Watanabe, Y., Kogi, K., Aihara, K. and Matsuda, A. Eur. J. Pharmacol. 196 (1991) 69; (c) Matsuda, A., Shinozaki, M., Yamaguchi, T., Homma, H., Nomoto, R., Miyasaka, T., Watanabe, Y. and Abiru, T. J. Med. Chem. 35 (1992) 241; (d) Jacobson, K. A., Shi, D., Gallo-Rodrigues, C., Manning, M., Jr., Müller, C., Daly, J. W., Neumeyer, J. L., Kiriasis, L. and Pfleiderer, W. J. Med. Chem. 36 (1993) 2639 and references therein; (e) Sági, G., Ötvös, L., Ikeda, S., Andrei, G., Snoeck, R. and De Clercq, E. J. Med. Chem. 37 (1994) 1307; (f) Estep, K. G., Josef, K. A., Bacon, E. R., Carabateas, P. M., Rumney, S., IV., Pilling, G. M., Krafte, D. S., Volberg, W. A., Dillon, K., Dugrenier, N., Briggs, G. M., Canniff, P. C., Gorczyca, W. P., Stankus, G. P. and Ezrin, A. M. J. Med. Chem. 38 (1995) 2582.
3. See for instance: (a) Montgomery, J. A. and Hewson, K. J. Med. Chem. 11 (1968) 49; (b) Abiru, T., Yamaguchi, T., Watanabe, Y., Kogi, K., Aihara, K. and Matsuda, A. Eur. J. Pharmacol. 196 (1991) 69; (c) Matsuda, A., Shinozaki, M., Yamaguchi, T., Homma, H., Nomoto, R., Miyasaka, T., Watanabe, Y. and Abiru, T. J. Med. Chem. 35 (1992) 241; (d) Jacobson, K. A., Shi, D., Gallo-Rodrigues, C., Manning, M., Jr., Müller, C., Daly, J. W., Neumeyer, J. L., Kiriasis, L. and Pfleiderer, W. J. Med. Chem. 36 (1993) 2639 and references therein; (e) Sági, G., Ötvös, L., Ikeda, S., Andrei, G., Snoeck, R. and De Clercq, E. J. Med. Chem. 37 (1994) 1307; (f) Estep, K. G., Josef, K. A., Bacon, E. R., Carabateas, P. M., Rumney, S., IV., Pilling, G. M., Krafte, D. S., Volberg, W. A., Dillon, K., Dugrenier, N., Briggs, G. M., Canniff, P. C., Gorczyca, W. P., Stankus, G. P. and Ezrin, A. M. J. Med. Chem. 38 (1995) 2582.
4. See for instance: (a) Montgomery, J. A. and Hewson, K. J. Med. Chem. 11 (1968) 49; (b) Abiru, T., Yamaguchi, T., Watanabe, Y., Kogi, K., Aihara, K. and Matsuda, A. Eur. J. Pharmacol. 196 (1991) 69; (c) Matsuda, A., Shinozaki, M., Yamaguchi, T., Homma, H., Nomoto, R., Miyasaka, T., Watanabe, Y. and Abiru, T. J. Med. Chem. 35 (1992) 241; (d) Jacobson, K. A., Shi, D., Gallo-Rodrigues, C., Manning, M., Jr., Müller, C., Daly, J. W., Neumeyer, J. L., Kiriasis, L. and Pfleiderer, W. J. Med. Chem. 36 (1993) 2639 and references therein; (e) Sági, G., Ötvös, L., Ikeda, S., Andrei, G., Snoeck, R. and De Clercq, E. J. Med. Chem. 37 (1994) 1307; (f) Estep, K. G., Josef, K. A., Bacon, E. R., Carabateas, P. M., Rumney, S., IV., Pilling, G. M., Krafte, D. S., Volberg, W. A., Dillon, K., Dugrenier, N., Briggs, G. M., Canniff, P. C., Gorczyca, W. P., Stankus, G. P. and Ezrin, A. M. J. Med. Chem. 38 (1995) 2582.
5. See for instance: (a) Montgomery, J. A. and Hewson, K. J. Med. Chem. 11 (1968) 49; (b) Abiru, T., Yamaguchi, T., Watanabe, Y., Kogi, K., Aihara, K. and Matsuda, A. Eur. J. Pharmacol. 196 (1991) 69; (c) Matsuda, A., Shinozaki, M., Yamaguchi, T., Homma, H., Nomoto, R., Miyasaka, T., Watanabe, Y. and Abiru, T. J. Med. Chem. 35 (1992) 241; (d) Jacobson, K. A., Shi, D., Gallo-Rodrigues, C., Manning, M., Jr., Müller, C., Daly, J. W., Neumeyer, J. L., Kiriasis, L. and Pfleiderer, W. J. Med. Chem. 36 (1993) 2639 and references therein; (e) Sági, G., Ötvös, L., Ikeda, S., Andrei, G., Snoeck, R. and De Clercq, E. J. Med. Chem. 37 (1994) 1307; (f) Estep, K. G., Josef, K. A., Bacon, E. R., Carabateas, P. M., Rumney, S., IV., Pilling, G. M., Krafte, D. S., Volberg, W. A., Dillon, K., Dugrenier, N., Briggs, G. M., Canniff, P. C., Gorczyca, W. P., Stankus, G. P. and Ezrin, A. M. J. Med. Chem. 38 (1995) 2582.
6. See for instance: (a) Montgomery, J. A. and Hewson, K. J. Med. Chem. 11 (1968) 49; (b) Abiru, T., Yamaguchi, T., Watanabe, Y., Kogi, K., Aihara, K. and Matsuda, A. Eur. J. Pharmacol. 196 (1991) 69; (c) Matsuda, A., Shinozaki, M., Yamaguchi, T., Homma, H., Nomoto, R., Miyasaka, T., Watanabe, Y. and Abiru, T. J. Med. Chem. 35 (1992) 241; (d) Jacobson, K. A., Shi, D., Gallo-Rodrigues, C., Manning, M., Jr., Müller, C., Daly, J. W., Neumeyer, J. L., Kiriasis, L. and Pfleiderer, W. J. Med. Chem. 36 (1993) 2639 and references therein; (e) Sági, G., Ötvös, L., Ikeda, S., Andrei, G., Snoeck, R. and De Clercq, E. J. Med. Chem. 37 (1994) 1307; (f) Estep, K. G., Josef, K. A., Bacon, E. R., Carabateas, P. M., Rumney, S., IV., Pilling, G. M., Krafte, D. S., Volberg, W. A., Dillon, K., Dugrenier, N., Briggs, G. M., Canniff, P. C., Gorczyca, W. P., Stankus, G. P. and Ezrin, A. M. J. Med. Chem. 38 (1995) 2582.
7. (a) Dammann, L. G., Leonard, N. J., Schmitz, R. Y. and Skoog, F. Phytochemistry 13 (1974) 329;
8. (b) Henderson, T. R., Frihart, C., Leonard, N. L., Schmitz, R. Y. and Skoog, F. Phytochemistry 14 (1975) 1687;
9. (c) Koyama, S., Kumazawa, Z., Kashimura, N. and Nishida, R. Agric. Biol. Chem. 49 (1985) 1859;
10. (d) Nishikawa, S., Kumazawa, Z., Mizutani, H. and Kondo, H. Agric. Biol. Chem. 49 (1985) 3353;
11. (e) Nishikawa, S., Kumazawa, Z., Mizutani, H. and Kashimura, N. Agric. Biol. Chem. 50 (1986) 1089.
12. See for instance: (a) Taylor, E. C. and Martin, S. F. J. Am. Chem. Soc. 96 (1974) 8095; (b) Hirota, K., Kitade, Y., Kanbe, Y. and Maki, Y. J. Org. Chem. 57 (1992) 5268; (c) Gundersen, L.-L., Bakkestuen, A. K., Aasen, A. J., Øverås, H. and Rise, F. Tetrahedron 50 (1994) 9743; (d) Gundersen, L.-L., Langli, G. and Rise, F. Tetrahedron Lett. 36 (1995) 1945; (e) Désaubry, L. and Bourguignon, J.-J. Tetrahedron Lett. 36 (1995) 7875; (f) Andresen, G., Gundersen, L.-L., Lundmark, M., Rise, F. and Sundell, S. Tetrahedron 51 (1995) 3655; (g) Dvoráková, H., Dvorák, D. and Holy, A. Tetrahedron Lett. 37 (1996) 1285; (h) Andresen, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 12979.
13. See for instance: (a) Taylor, E. C. and Martin, S. F. J. Am. Chem. Soc. 96 (1974) 8095; (b) Hirota, K., Kitade, Y., Kanbe, Y. and Maki, Y. J. Org. Chem. 57 (1992) 5268; (c) Gundersen, L.-L., Bakkestuen, A. K., Aasen, A. J., Øverås, H. and Rise, F. Tetrahedron 50 (1994) 9743; (d) Gundersen, L.-L., Langli, G. and Rise, F. Tetrahedron Lett. 36 (1995) 1945; (e) Désaubry, L. and Bourguignon, J.-J. Tetrahedron Lett. 36 (1995) 7875; (f) Andresen, G., Gundersen, L.-L., Lundmark, M., Rise, F. and Sundell, S. Tetrahedron 51 (1995) 3655; (g) Dvoráková, H., Dvorák, D. and Holy, A. Tetrahedron Lett. 37 (1996) 1285; (h) Andresen, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 12979.
14. See for instance: (a) Taylor, E. C. and Martin, S. F. J. Am. Chem. Soc. 96 (1974) 8095; (b) Hirota, K., Kitade, Y., Kanbe, Y. and Maki, Y. J. Org. Chem. 57 (1992) 5268; (c) Gundersen, L.-L., Bakkestuen, A. K., Aasen, A. J., Øverås, H. and Rise, F. Tetrahedron 50 (1994) 9743; (d) Gundersen, L.-L., Langli, G. and Rise, F. Tetrahedron Lett. 36 (1995) 1945; (e) Désaubry, L. and Bourguignon, J.-J. Tetrahedron Lett. 36 (1995) 7875; (f) Andresen, G., Gundersen, L.-L., Lundmark, M., Rise, F. and Sundell, S. Tetrahedron 51 (1995) 3655; (g) Dvoráková, H., Dvorák, D. and Holy, A. Tetrahedron Lett. 37 (1996) 1285; (h) Andresen, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 12979.
15. See for instance: (a) Taylor, E. C. and Martin, S. F. J. Am. Chem. Soc. 96 (1974) 8095; (b) Hirota, K., Kitade, Y., Kanbe, Y. and Maki, Y. J. Org. Chem. 57 (1992) 5268; (c) Gundersen, L.-L., Bakkestuen, A. K., Aasen, A. J., Øverås, H. and Rise, F. Tetrahedron 50 (1994) 9743; (d) Gundersen, L.-L., Langli, G. and Rise, F. Tetrahedron Lett. 36 (1995) 1945; (e) Désaubry, L. and Bourguignon, J.-J. Tetrahedron Lett. 36 (1995) 7875; (f) Andresen, G., Gundersen, L.-L., Lundmark, M., Rise, F. and Sundell, S. Tetrahedron 51 (1995) 3655; (g) Dvoráková, H., Dvorák, D. and Holy, A. Tetrahedron Lett. 37 (1996) 1285; (h) Andresen, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 12979.
16. See for instance: (a) Taylor, E. C. and Martin, S. F. J. Am. Chem. Soc. 96 (1974) 8095; (b) Hirota, K., Kitade, Y., Kanbe, Y. and Maki, Y. J. Org. Chem. 57 (1992) 5268; (c) Gundersen, L.-L., Bakkestuen, A. K., Aasen, A. J., Øverås, H. and Rise, F. Tetrahedron 50 (1994) 9743; (d) Gundersen, L.-L., Langli, G. and Rise, F. Tetrahedron Lett. 36 (1995) 1945; (e) Désaubry, L. and Bourguignon, J.-J. Tetrahedron Lett. 36 (1995) 7875; (f) Andresen, G., Gundersen, L.-L., Lundmark, M., Rise, F. and Sundell, S. Tetrahedron 51 (1995) 3655; (g) Dvoráková, H., Dvorák, D. and Holy, A. Tetrahedron Lett. 37 (1996) 1285; (h) Andresen, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 12979.
17. See for instance: (a) Taylor, E. C. and Martin, S. F. J. Am. Chem. Soc. 96 (1974) 8095; (b) Hirota, K., Kitade, Y., Kanbe, Y. and Maki, Y. J. Org. Chem. 57 (1992) 5268; (c) Gundersen, L.-L., Bakkestuen, A. K., Aasen, A. J., Øverås, H. and Rise, F. Tetrahedron 50 (1994) 9743; (d) Gundersen, L.-L., Langli, G. and Rise, F. Tetrahedron Lett. 36 (1995) 1945; (e) Désaubry, L. and Bourguignon, J.-J. Tetrahedron Lett. 36 (1995) 7875; (f) Andresen, G., Gundersen, L.-L., Lundmark, M., Rise, F. and Sundell, S. Tetrahedron 51 (1995) 3655; (g) Dvoráková, H., Dvorák, D. and Holy, A. Tetrahedron Lett. 37 (1996) 1285; (h) Andresen, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 12979.
18. See for instance: (a) Taylor, E. C. and Martin, S. F. J. Am. Chem. Soc. 96 (1974) 8095; (b) Hirota, K., Kitade, Y., Kanbe, Y. and Maki, Y. J. Org. Chem. 57 (1992) 5268; (c) Gundersen, L.-L., Bakkestuen, A. K., Aasen, A. J., Øverås, H. and Rise, F. Tetrahedron 50 (1994) 9743; (d) Gundersen, L.-L., Langli, G. and Rise, F. Tetrahedron Lett. 36 (1995) 1945; (e) Désaubry, L. and Bourguignon, J.-J. Tetrahedron Lett. 36 (1995) 7875; (f) Andresen, G., Gundersen, L.-L., Lundmark, M., Rise, F. and Sundell, S. Tetrahedron 51 (1995) 3655; (g) Dvoráková, H., Dvorák, D. and Holy, A. Tetrahedron Lett. 37 (1996) 1285; (h) Andresen, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 12979.
19. See for instance: (a) Taylor, E. C. and Martin, S. F. J. Am. Chem. Soc. 96 (1974) 8095; (b) Hirota, K., Kitade, Y., Kanbe, Y. and Maki, Y. J. Org. Chem. 57 (1992) 5268; (c) Gundersen, L.-L., Bakkestuen, A. K., Aasen, A. J., Øverås, H. and Rise, F. Tetrahedron 50 (1994) 9743; (d) Gundersen, L.-L., Langli, G. and Rise, F. Tetrahedron Lett. 36 (1995) 1945; (e) Désaubry, L. and Bourguignon, J.-J. Tetrahedron Lett. 36 (1995) 7875; (f) Andresen, G., Gundersen, L.-L., Lundmark, M., Rise, F. and Sundell, S. Tetrahedron 51 (1995) 3655; (g) Dvoráková, H., Dvorák, D. and Holy, A. Tetrahedron Lett. 37 (1996) 1285; (h) Andresen, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 12979.
20. (a) Van Aerschot, A. A., Mamos, P., Weyns, N. J., Ikeda, S., De Clercq, E. and Herdewijn, P. A. J. Med. Chem. 36 (1993) 2938;
21. (b) Manfredini, S., Baraldi, P. G., Bazzanini, R., Marangoni, M., Simoni, D., Balzarini, J. and De Clercq, E. J. Med Chem. 38 (1995) 199;
22. (c) Langli, G., Gundersen, L.-L. and Rise, F. Tetrahedron 52 (1996) 5625.
23. See for instance: (a) Bergmann, E. D., Ginsburg, D. and Pappo, R. Org. React. 10 (1959) 179, and references therein; (b) Danishefsky, S., Cain, P, and Nagel, A. J. Am. Chem. Soc. 97 (1975) 380.
24. See for instance: (a) Bergmann, E. D., Ginsburg, D. and Pappo, R. Org. React. 10 (1959) 179, and references therein; (b) Danishefsky, S., Cain, P, and Nagel, A. J. Am. Chem. Soc. 97 (1975) 380.
25. (a) Nagatsugi, F., Uemura, K., Nakashima, S., Maeda, M. and Sasaki, S. Tetrahedron Lett. 36 (1995) 421;
26. (b) Czernecki, S., Hoang, A. and Valéry, J.-M. Tetrahedron Lett. 37 (1996) 8857.
27. Øverås, A. T., Gundersen, L.-L. and Rise, F. Tetrahedron 53 (1997) 1777.
28. Gundersen, L.-L. Acta Chem. Scand. 50 (1996) 58.
29. (a) Albert, A. and Hampton, A. J. Chem. Soc. (1952) 4985;
30. (b) Holland, A. Chem. Ind. (London) 73 (1954) 786;
31. (c) Jerchel, D. and Heck, H. E. Justus Liebigs Ann. Chem. 613 (1958) 171.
32. Hampton, A. J. Heterocycl. Chem. 11 (1974) 255.
33. Jung, M. E. In: Trost, B. M. and Flemimg, I., Eds., Comprehensive Organic Synthesis, Vol. 4, pp. 3-4, Pergamon, Oxford 1991.
34. Kitayama, T. Tetrahedron 52 (1996) 6139.
35. See for instance: (a) Fedorynski, M., Wojciechowski, K., Matacz, Z. and Makosza, M. J. Org. Chem. 43 (1978) 4682; (b) Ernst, H., Ottow, E., Recker, H. G. and Winterfeldt, E. Chem. Ber. 114 (1981) 1907.
36. See for instance: (a) Fedorynski, M., Wojciechowski, K., Matacz, Z. and Makosza, M. J. Org. Chem. 43 (1978) 4682; (b) Ernst, H., Ottow, E., Recker, H. G. and Winterfeldt, E. Chem. Ber. 114 (1981) 1907.