Radical decarboxylative alkylation onto heteroaromatic bases with trivalent iodine compounds

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 20, 1993, Pages 2417-2427

  Togo, Hideo ^a   Aoki, Masahiko ^a   Kuramochi, Tadashi ^a   Yokoyama, Masataka ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049071931     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19930002417     Document Type: Article

References (64)

1. A. Varvoglis, Synthesis, 1984,709;
2. M. Ochiai and Y. Nagao, J. Synth. Org. Chem. Jpn., 1986,44, 660;
3. T. Umemoto, J. Synth. Org. Chem. Jpn., 1983,41,251;
4. R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431;
5. R. M. Moriarty, R. K. Vaid and G. F. Koser, Synlett, 1990,365;
6. G. F. Koser, Hypervalent Halogen Compounds (ch. 18) in The Chemistry of Functional Groups, Supplement D, eds. S. Patai and Z. Rappoport, Wiley, New York, 1983.
7. G. Lukacs and M. Ohno, Recent Progress in the Chemical Synthesis of Antibiotics, Springer-Verlag, Berlin, 1990.
8. B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986, ch. 5;
9. F. Minisci, E. Vismara and F. Fontana, Heterocycles, 1989,28,489;
10. F. Fontana, F. Minisci, M. C. N. Barbosa and E. Vismara, J. Org. Chem., 1991,56,2866;
11. F. Minisci, E. Vismara and F. Fontana, J.Heterocycl. Chem., 1990,27, 79.
12. (a)J. E. Lefflerand L. J. Story, J.Am. Chem. SOC., 1967,89,2333;
13. J. E. Leffler,D. C. Ward, and A. Burduroglu, J. Am. Chem. SOC., 1972,94, 5339;
14. (b)J. I. Concepcion, C. G. Francisco, R. Freire, R. Hernandez, J. A. Salazar and E. Suarez, J. Org. Chem., 1986,51,402;
15. R. Singh and G. Just, Synth. Commun., 1988,18, 1327;
16. (c)M. Karelsky and K. H. Pausacker, Aust. J. Chem., 1958, 11, 39;
17. F. Minisci, E. Vismara, F. Fontana and M. C. N. Barbosa, Tetrahedron Lett., 1989,30,4569;
18. J. E. Leffler, W. J. M. Mitchell and B. C. Menon, J. Org. Chem., 1966, 31,1153;
19. B. M. Lynch and K. H. Pausacker, Aust. J. Chem., 1957,10, 329;
20. D. H. Hey, C. J. M. Stirling and G. H. Williams, J. Chem. SOC., 1956, 1475;
21. (d)M. Tingoli, M. Tiecco, D. Chianelli, R. Balducci and A. Temperini, J. Org. Chem., 1991, 56, 6809;
22. (e)R. Hernandez, J. J. Marrero and E. Suarez, Tetrahedron Lett., 1989,30,5501;
23. K. Furuta, T. Nagata and H. Yamamoto, Tetrahedron Lett., 1988,29,2215;
24. P. Galatsis and S. D. Millan, Tetrahedron Lett., 1991,32, 7493;
25. C. W. Ellwood and G. Pattenden, Tetrahedron Lett., 1991, 32, 1591;
26. R. Hernandez, J. J. Marrero and E. Suarez, Tetrahedron Lett., 1988,29, 5979;
27. C. G. Francisco, R. Freire, M. S. Rodriguez and E. Suarez, Tetrahedron Lett., 1987,28,3397;
28. M. A. Brimble, G. M. Williams, R. Baker and M. James, Tetrahedron Lett., 1990,31,3043;
29. R. Freire, R. Hernandez, M. S. Rodriguez and E. Suarez, Tetrahedron Lett., 1987, 28, 981;
30. J. I. Concepcion, C. G. Francisco, R. Hernandez, J. A. Salazar and E. Suarez, Tetrahedron Lett., 1984,25, 1953;
31. R. Freire, J. J. Marrero, M. S. Rodriquez and E. Suarez, Tetrahedron Lett., 1986, 27, 383;
32. A. Boto, C. Betancor, T. Prange and E. Suarez, Tetrahedron Lett., 1992, 33, 6687;
33. (f)P. Armas, R. Carrau, J. I. Concepcion, C. G. Francisco, R. Hernandez and E. Suarez, Tetrahedron Lett., 1985,26,2493.
34. H. Togo, M. Aoki and M. Yokoyama, Tetrahedron Lett., 1991,32, 6559;
35. Chem. Lett., 1991, 1691.
36. (a) D. H. R. Barton, D. Crich and W. B. Motherwell, Tetrahedron, 1985,41,3901;
37. D. H. R. Barton, Aldrichim. Acta, 1990,23,3;
38. D. Crich and L. Quintero, Chem. Rev., 1989, 89, 1413 and references cited therein;
39. (b)M. Hasebe and T. Tsuchiya, Tetrahedron Lett., 1986,27, 3239;
40. M. Hasebe, K. Kogawa and T. Tsuchiya, Tetrahedron Lett., 1984,25,3887;
41. H. Hasebe and T. Tsuchiya, Tetrahedron Lett., 1987, 28, 6207;
42. (c) K. Okada, K. Okubo and M. Oda, Tetrahedron Lett., 1989,30,6733;
43. A. Sugimori and T. Yamada, Bull. Chem. SOC. Jpn., 1986, 59, 391 1;
44. (d) K. Okada, K. Okamoto and M. Oda, J. Am. Chem. SOC., 1988,110,8736;
45. K. Okada, K. Okamoto, N. Morita, K. Okubo and M. Oda, J. Am. Chem. SOC., 1991,113,9401.
46. P. J. Stang, M. Boehshar, H.Wingert and T. Kitamura, J. Am. Chem. SOC.,1988, 110, 3272;
47. E. B. Merkushev, A. N. Novikov, S. S. J. CHEM. SOC. PERKIN TRANS. 1 1993 Makarchenko, A. S.Moskalchuk, V. V. Glushkova, T. I. Kogai and L. G. Polyakova, Zh. Org. aim., 1975,11, 1259.
48. H. OguraandH. Takahashi, J.Synth. Org. Chem. Jpn., 1980,38,756;
49. H. OguraandH. Takahashi, J.Synth. Org. Chem. Jpn., 1980,38,756;
50. H. OguraandH. Takahashi, J.Synth. Org. Chem. Jpn., 1980,38,756;
51. J. G. Buchanan, Fortschr. Chem. Org. Naturst., 1983, 44, 243;
52. U. Hacksell and G. D. Daues, Prog. Med. Chem., 1985,33,1;
53. K. A. Watanabe, J. Synth. Org. Chem. Jpn., 1987, 45, 212;
54. N. Katagiri, J. Synth. Org. Chem. Jpn., 1989,47, 707.
55. H. Togo, M. Fujii, T. Ikuma and M. Yokoyama, Tetrahedron Lett., 1991,32,3377.
56. E. Vismara, G. Torri, N. Pastori and M. Marchiandi, Tetrahedron Lett., 1992,33, 7575.
57. D. H. R. Barton and S. W. McCombie, J. Chem. SOC.,Perkin Trans. I, 1975, 1574;
58. D. H. R. Barton, W. B. Motherwell and A. Stange, Synthesis, 1981, 743;
59. D. H. R. Barton, W. Hartwig, R. S. Hay-Motherwell, W. B. Motherwell and A. Stange, Tetrahedron Lett., 1982,23,2019;
60. D. H. R. Barton and J. Cs. Jaszberenyi, Tetrahedron Lett., 1989,30,2619;
61. S. C. Dolan and J. MacMillan, J. Chem. SOC., Chem. Commun., 1985,1588;
62. M. H. Beale, P. Gaskin, P. S. Kirkwood and J. MacMillan, J. Chem. Soc., Perkin Trans. I, 1980, 885;
63. Z. J. Duri, B. M. Fraga, A. G. Gonzaley, J. R. Hanson and F. G. Tellado, J. Chem. Soc., Perkin Trans. I, 1984, 1 109.
64. M. Schmeisser, K. Dahmen and P. Sartori, Chem. Ber., 1967, 100, 1633.