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Synthesis of 4-aminopolymethoxycoumarins from 4-hydroxycoumarin triflates

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Abstract

4-Aminocoumarins were synthesized in high yields by the reaction of 4-hydroxycoumarin trifluoromethanesulfonates with amines.

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References

  1. F. Borges, F. Roleira, N. Milhazes, L. Santana, and E. Uriarte, Curr. Med. Chem., 2005, 12, 887; R. D. H. Murray, J. Mendez, and S. A. Brown, The Natural Coumarins. Ocurrence and Biochemistry, J. Wiley and Sons, Chichester, 1982, 714 pp.; Coumarins, Biology. Applications and Mode of Action, Eds R. O’ Kennedy and R. D. Thornes, J. Wiley and Sons, Chichester, 1997, 348 pp.; V. M. Malikov and A. I. Saidkhodzhaev, Chem. Nat. Compd., 1998, 34, 202; E. Albengres, H. Le Louet, and J. P. Tillement, Drug Safety, 1998, 18, 83; S. Sardari, S. Nishibe, and M. Daneshtalab, Stud. Nat. Prod. Chem., 2000, 23, 335.

    Article  CAS  Google Scholar 

  2. L. Schio, F. Chatreaux, and M. Klich, Tetrahedron Lett., 2000, 41, 1543.

    Article  CAS  Google Scholar 

  3. A. R. Quesada, M. D. G. Gravalos, and J. L. F. Puentes, Br. J. Cancer, 1996, 74, 677; H. Kang and W. Fenical, J. Org. Chem., 1997, 62, 3254; D. L. Boger, C. W. Boyce, M. A. Labroli, C. A. Schon, and Q. Jin, J. Am. Chem. Soc., 1999, 121, 54.

    CAS  Google Scholar 

  4. M. V. R. Reddy, M. R. Rao, D. Rhodes, M. S. T. Hansen, K. Rubins, F. D. Bushman, Y. Venkateswarlu, and D. J. Faulkner, J. Med. Chem., 1999, 42, 163.

    Google Scholar 

  5. P. R. Kym, R. Iyengar, A. J. Souers, J. K. Lynch, A. S. Judd, J. Gao, J. Freeman, M. Mulhern, G. Zhao, A. Vasudevan, D. Wodka, C. Blackburn, J. Brown, J. L. Che, C. Cullis, S. J. Lai, M. J. LaMarche, T. Marsilje, J. Roses, T. Sells, B. Geddes, E. Govek, M. Patane, D. Fry, B. D. Dayton, S. Brodjian, D. Falls, M. Brune, E. Bush, R. Shapiro, V. Knourek-Segel, T. Fey, C. McDowell, G. A. Reinhart, L. C. Preusser, K. Marsh, L. Hernandez, H. L. Sham, and C. A. Collins, J. Med. Chem., 2005, 48, 5888.

    Article  CAS  Google Scholar 

  6. C. A. Kontogiorgis and D. J. Hadjipavlou-Litina, J. Med. Chem., 2005, 48, 6400.

    Article  CAS  Google Scholar 

  7. R. J. Griffin, G. Fontana, B. T. Golding, S. Guiard, I. R. Hardcastle, J. J. J. Leahy, N. Martin, C. Richardson, L. Rigoreau, M. Stockley, and G. C. M. Smith, J. Med. Chem., 2005, 48, 569.

    Article  CAS  Google Scholar 

  8. A. Huwe, R. Mazitschek, and A. Giannis, Angew. Chem., Int. Ed. Engl., 2003, 42, 2122; K. W. Wood, W. D. Cornwell, and J. R. Jackson, Curr. Opinion in Pharmacology, 2001, 1, 370.

    Article  CAS  Google Scholar 

  9. G. V. Grishina, A. A. Borisenko, Z. G. Nosan’, L. D. Ashkinadze, I. S. Veselov, N. S. Zefirov, E. V. Karamov, and G. V. Kornilaeva, Dokl. Akad. Nauk, 2003, 391, 487 [Dokl. Chem., 2003, 391, 195 (Engl. Transl.)].

    Google Scholar 

  10. C. Bailly, C. Bal, P. Barbier, S. Combes, J.-P. Finet, M.-P. Hildebrand, V. Peyrot, and N. Wattez, J. Med. Chem., 2003, 46, 5437; (b) I. P. Beletskaya, O. G. Ganina, A. V. Tsvetkov, A. Yu. Fedorov, and J.-P. Finet, Synlett, 2004, 15, 2797.

    Article  CAS  Google Scholar 

  11. V. A. Zagorevskii, V. L. Savel’ev, and L. M. Meshcheryakova, Khim. Geterotsikl. Soedin., 1970, 1019 [Chem. Heterocycl. Compd., 1970, 947 (Engl. Transl.)].

  12. O. H. Hishmat, A. M. Gohar, M. E. Wassef, M. R. Shalash, and I. Ismail, Pharm. Acta Helv., 1977, 52, 252.

    CAS  Google Scholar 

  13. E. V. Stoyanov and I. C. Ivanov, Molecules, 2004, 9, 627.

    Article  CAS  Google Scholar 

  14. G. V. Grishina, A. A. Borisenko, I. S. Veselov, and A. M. Petrenko, Zh. Org. Khim., 2005, 41, 281 [Russ. J. Org. Chem., 2005, 41, 272 (Engl. Transl.)].

    Google Scholar 

  15. D. H. R. Barton, D. M. X. Donnelly, J.-P. Finet, and P. J. Guiry, J. Chem. Soc., Perkin Trans. 1, 1992, 1365; G. M. Boland, D. M. X. Donnelly, J.-P. Finet, and M. D. Rea, J. Chem. Soc., Perkin Trans. 1, 1996, 2591; S. Combes, J.-P. Finet, and D. Siri, J. Chem. Soc., Perkin Trans. 1, 2002, 38.

  16. V. L. Savel’ev, O. S. Artamonova, V. S. Troitskaya, V. V. Shavyrina, T. G. Afanas’eva, and V. A. Zagorevskii, Khim. Geterotsikl. Soedin., 1982, 18, 896 [Chem. Heterocycl. Compd., 1982, 18, 676 (Engl. Transl.)].

    Google Scholar 

  17. D. P. Spalding, H. S. Mosher, and F. C. Whitmore, J. Am. Chem. Soc., 1950, 72, 5338.

    Article  CAS  Google Scholar 

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1583–1588, September, 2006.

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Ganina, O.G., Veselov, I.S., Grishina, G.V. et al. Synthesis of 4-aminopolymethoxycoumarins from 4-hydroxycoumarin triflates. Russ Chem Bull 55, 1642–1647 (2006). https://doi.org/10.1007/s11172-006-0467-9

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  • DOI: https://doi.org/10.1007/s11172-006-0467-9

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