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Results: Developments of New Radical Cascades with N-Acylcyanamides

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Development of New Radical Cascades and Multi-Component Reactions

Part of the book series: Springer Theses ((Springer Theses))

Abstract

Since radical cascades using cyanamides have been reported only starting from aryl radicals, we have wished to broaden the scope of these cascades. Our objectives were to test the reactivity of alkyl, vinyl and aminyl radicals in this process. Indeed, the use of alkyl and vinyl radical should provide us with a straightforward access to natural and biologically active quinazolinones; while the use of aminyl radicals should afford the first radical synthesis of guanidines.

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References

  1. Amin, A. H., & Mehta, D. R. (1959). Nature, 183, 1317–1318.

    Article  Google Scholar 

  2. Al-Shamma, A., Drake, S., Flynn, D. L., Mitscher, L. A., Park, Y. H., Rao, G. S. R., et al. (1981). Journal of Natural Products, 44, 745–747.

    Article  CAS  Google Scholar 

  3. Mori, M., Kobayashi, H., Kimura, M., & Ban, Y. (1997). Heterocycles, 46, 541–543.

    Article  Google Scholar 

  4. Akazome, M., Kondo, T., & Watanabe, Y. (1993). Journal of Organic Chemistry, 58, 310–312.

    Article  CAS  Google Scholar 

  5. Takeuchi, H., Hagiwara, S., & Eguchi, S. (1989). Tetrahedron, 45, 6375–6378.

    Article  CAS  Google Scholar 

  6. Bowman, W. R., Elsegood, M. R. J., Stein, T., & Weaver, G. W. (2007). Organic & Biomolecular Chemistry, 5, 103–113.

    Article  CAS  Google Scholar 

  7. Johns, S. R., & Lamberton, J. A. (1965). Chemical Communications, 267–269.

    Google Scholar 

  8. Hart, N. K., Johns, S. R., & Lamberton, J. A. (1971). Australian Journal of Chemistry, 24, 223–224.

    Article  CAS  Google Scholar 

  9. Liu, J. F., Wilson, C. J., Ye, P., Sprague, K., Sargent, K., Si, Y., et al. (2006). Bioorganic & Medicinal Chemistry Letters, 16, 686–690.

    Article  CAS  Google Scholar 

  10. Hermecz, I., Vasvari-Debreczy, L., Horvath, A., Balogh, M., Kökösi, J., DeVos, C., et al. (1987). Journal of Medicinal Chemistry, 30, 1543–1549.

    Article  CAS  Google Scholar 

  11. Elmuradov, B. Z., & Shakhidoyatov, K. M. (2004). Chem. Nat. Comp., 40, 496–498.

    Article  CAS  Google Scholar 

  12. Minin, P. L., & Walton, J. C. (2003). Journal of Organic Chemistry, 68, 2960–2963.

    Article  CAS  Google Scholar 

  13. Bowman, W. R., Stephenson, P. T., Terrett, N. K., & Young, A. R. (1995). Tetrahedron, 51, 7959–7980.

    Article  CAS  Google Scholar 

  14. Servais, A., Azzouz, M., Lopes, D., Courillon, C., & Malacria, M. (2007). Angewandte Chemie International Edition, 46, 576–579.

    Article  CAS  Google Scholar 

  15. Cockerill, A. F., Deacon, A., Harrison, R. G., Osborne, D. J., Prime, D. M., & Ross, W. J., et al. (1976). Synthesis-Stuttgart, 591–593.

    Google Scholar 

  16. Munbunjong, W., Lee, E. H., Chavasiri, W., & Jang, D. O. (2005). Tetrahedron Letters, 46, 8769–8771.

    Article  CAS  Google Scholar 

  17. Coulomb, J., Certal, V., Larraufie, M.-H., Ollivier, C., Corbet, J.-P., Mignani, G., et al. (2009). Chemistry–A European Journal, 15, 10225–10232.

    Article  CAS  Google Scholar 

  18. Shanks, D., Berlin, S., Besev, M., Ottosson, H., & Engman, L. (2004). Journal of Organic Chemistry, 69, 1487–1491.

    Article  CAS  Google Scholar 

  19. Larraufie, M.-H., Malacria, M., Courillon, C., Ollivier, C., Fensterbank, L., & Lacôte, E. (2013). Tetrahedron. doi:10.1016. Copyright 2013 Elsevier (in press).

    Google Scholar 

  20. Wu, X., Qin, G., Cheung, K. K., & Cheng, K. F. (1997). Tetrahedron, 53, 13323–13328.

    Article  CAS  Google Scholar 

  21. Molina, P., Tarraga, A., Gonzales-Tejero, A., Rioja, I., Ubeda, A., Terencio, M. C., et al. (2001). Natural Products, 64, 1297–1300.

    Article  CAS  Google Scholar 

  22. Sugiyama, H., Yokokawa, F., & Shiori, T. (2000). Organic Letters, 14, 2149–2152.

    Article  Google Scholar 

  23. Klopp, A. H., & Wright, G. F. (1939). Journal of Organic Chemistry, 4, 142–149.

    Article  CAS  Google Scholar 

  24. Mc Elvain, S. M., & Mc Leish, W. L. (1955). Journal of the American Chemical Society, 77, 3786–3789.

    Article  CAS  Google Scholar 

  25. Iwai, I., Iwashige, T., Yura, R., Nakamura, N., & Shinozaki, K. (1964). Chemical & Pharmaceutical Bulletin, 12, 1446–1451.

    Article  CAS  Google Scholar 

  26. Mayo, F. R. (1968). Journal of the American Chemical Society, 90, 1289–1295.

    Article  CAS  Google Scholar 

  27. Chong, Y. K., Rizzardo, E., & Solomon, D. H. (1983). Journal of the American Chemical Society, 105, 7761–7762.

    Article  CAS  Google Scholar 

  28. Walton, J. C., & Studer, A. (2005). Accounts of Chemical Research, 38, 794–802.

    Article  CAS  Google Scholar 

  29. Zytowski, T., & Fischer, H. (1997). Journal of the American Chemical Society, 119, 12669–12878.

    Article  Google Scholar 

  30. Stefani, A. P., & Szwarc, M. (1962). Journal of the American Chemical Society, 84, 3661–3666.

    Article  CAS  Google Scholar 

  31. Whittemore, I. M., Stefani, A. P., & Szwarc, M. (1962). Journal of the American Chemical Society, 84, 3799–3803.

    Article  CAS  Google Scholar 

  32. Dolbier, W. R, Jr. (2005). J. Fluor. Chem., 126, 157–163.

    Article  CAS  Google Scholar 

  33. Bégué, J. P., & Bonnet-Delpon, D. (2006). J. Fluor. Chem., 127, 992–1012.

    Article  Google Scholar 

  34. Kirk, K. L. (2006). J. Fluor. Chem., 127, 1013–1029.

    Article  CAS  Google Scholar 

  35. Billard T, & Langlois B. R. (2007). European Journal of Organic Chemistry, 891–897.

    Google Scholar 

  36. Ma, J.-A., & Cahard, D. (2004). Chemical Reviews, 104, 6119–6146.

    Article  CAS  Google Scholar 

  37. Bertrand, F., Pevere, V., Quiclet-Sire, B., & Zard, S. Z. (2001). Organic Letters, 3, 1069–1071. References therein.

    Article  CAS  Google Scholar 

  38. Larraufie, M.-H., Pellet, R., Fensterbank, L., Goddard, J.-P., Lacôte, E., Malacria, M., et al. (2011). Angewandte Chemie International Edition, 50, 4463–4466.

    Article  CAS  Google Scholar 

  39. Musa, O. M., Horner, J. H., Shahin, H., & Newcomb, M. (1996). Journal of the American Chemical Society, 118, 3862–3868.

    Article  CAS  Google Scholar 

  40. Hart, N. K., Johns, S. R., & Lamberton, J. A. (1969). Chemical Communications, 1484–1485.

    Google Scholar 

  41. Palmblad, J., et al. (2008). International Journal of Medicine and Science, 5, 87–91.

    Article  CAS  Google Scholar 

  42. Kashman, Y., Hirsh, S., McConnell, O. J., Ohtani, I., Kusumi, T., & Kakisawa, H. (1989). Journal of the American Chemical Society, 111, 8925–8926.

    Article  CAS  Google Scholar 

  43. Blondeau, P., Segura, M., Perez-Fernandez, R., & de Mendoza, J. (2007). Chemical Society Reviews, 36, 198–210.

    Article  CAS  Google Scholar 

  44. Galan, A., Andreu, D., Echavarren, A. M., Prados, P., & de Mendoza, J. (1992). Journal of the American Chemical Society, 114, 1511–1512.

    Article  CAS  Google Scholar 

  45. Ishikawa, T., & Isobe, T. (2002). Chemistry–A European Journal, 8, 553–557.

    Google Scholar 

  46. Corey, E. J., & Grogan, M. J. (1999). Organic Letters, 1, 157–160.

    Article  CAS  Google Scholar 

  47. Zard, S. Z. (2008). Chemical Society Reviews, 37, 1603–1618.

    Article  CAS  Google Scholar 

  48. Baralle, A., Baroudi, A., Daniel, M., Fensterbank, L., Goddard, J.-P., & Lacôte, E., et al. (2012). In C. Chatgilialoglu & A. Studer (Eds.), Encyclopedia of radicals in chemistry, biology and materials. New York: Wiley.

    Google Scholar 

  49. Heuger, G., Kalsow, S., & Göttlich, R. (2002). European Journal of Organic Chemistry, 11, 1848–1854.

    Article  Google Scholar 

  50. Noack, M., & Göttlich, R. (2002). Chemical Communications, 536–537.

    Google Scholar 

  51. Kemper, J., & Studer, A. (2005). Angewandte Chemie International Edition, 44, 4914–4917.

    Article  CAS  Google Scholar 

  52. Newcomb, M., Marquardt, D. J., & Deeb, T. M. (1990). Tetrahedron, 46, 2329–2344.

    Article  CAS  Google Scholar 

  53. Liu, F., Liu, K., Yuan, X., & Li, C. (2007). Journal of Organic Chemistry, 72, 10231–10234.

    Article  CAS  Google Scholar 

  54. Sherman, E. S., Chemler, S. R., Boon Tan, T., & Gerlits, O. (2004). Organic Letters, 6, 1573–1575.

    Article  CAS  Google Scholar 

  55. Chemler, S. R., & Fuller, P. H. (2007). Chemical Society Reviews, 36, 1153–1160.

    Article  CAS  Google Scholar 

  56. Minozzi, M., Nanni, D., & Spagnolo, P. (2009). Chemistry–A European Journal, 15, 7830–7840.

    Article  CAS  Google Scholar 

  57. Benati, L., Bencivenni, G., Leardini, R., Minozzi, M., Nanni, D., Scialpi, R., et al. (2004). Organic Letters, 6, 417–420.

    Article  CAS  Google Scholar 

  58. Lee, J. W., Jun, S. I., & Kim, K. (2001). Tetrahedron Letters, 42, 2709–2711.

    Article  CAS  Google Scholar 

  59. Wannaporn, D., & Ishikawa, T. (2005). Molecular Diversity, 9, 321–331.

    Article  CAS  Google Scholar 

  60. Hall, J. H., & Patterson, E. (1967). Journal of the American Chemical Society, 89, 5856–5961.

    Article  CAS  Google Scholar 

  61. Ha, C., Musa, O. M., Martinez, F. N., & Newcomb, M. (1997). Journal of Organic Chemistry, 62, 2704–2710.

    Article  CAS  Google Scholar 

  62. Demko, Z., & Sharpless, K. B. (2001). Organic Letters, 3, 4091–4094.

    Article  CAS  Google Scholar 

  63. Chen, Y., Kamlet, A. S., Steinman, J. B., & Liu, D. R. (2011). Nature Chem, 3, 146–153.

    Google Scholar 

  64. Larraufie, M.-H., Ollivier, C., Fensterbank, L., Malacria, M., & Lacôte, E. (2010). Angewandte Chemie International Edition, 49, 2178–2181.

    Article  CAS  Google Scholar 

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  1. Stockwell laboratory, Department of Biological Sciences, Columbia University, 550 West 120th Street, New York, NY, 10027, USA

    Marie-Hélène Larraufie

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  1. Marie-Hélène Larraufie
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Correspondence to Marie-Hélène Larraufie .

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Larraufie, MH. (2014). Results: Developments of New Radical Cascades with N-Acylcyanamides. In: Development of New Radical Cascades and Multi-Component Reactions. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-01324-4_2

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