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Ethynylindoles and their derivatives. Methods of synthesis and chemical transformations (review)

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Chemistry of Heterocyclic Compounds Aims and scope

The review contains data on methods for the production of ethynylindoles and their derivatives. The whole range of transformations of these compounds is examined in detail. It is demonstrated that indoles containing highly unsaturated groups are interesting not only as subjects for fundamental researches but can also be used successfully for the solution of various practical tasks.

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References

  1. A. B. Kamenskii, Yu. I. Smushkevich, N. N. Suvorov, and A. I. Livshits, Zh. Org. Khim., 16, 758 (1980).

    CAS  Google Scholar 

  2. A. B. Kamenskii, Yu. I. Smushkevich, A. I. Livshits, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 956 (1980). [Chem. Heterocycl. Comp., 16, 741 (1980)].

    Google Scholar 

  3. T. A. Prikhod’ko, S. F. Vasilevskii, and M. S. Shvartsberg, Izv. Akad. Nauk SSSR, Ser. Khim., 2602 (1984).

  4. T. A. Prikhod’ko, V. M. Kurilenko, Zh. N. Khlienko, S. F. Vasilevskii, and M. S. Shvartsberg, Izv. Akad. Nauk SSSR, Ser. Khim., 134 (1990).

  5. C. Saá, D. D. Crotts, G. Hsu, and K. P. C. Vollhardt, Synlett, 487 (1994).

  6. G. Abbiati, E. M. Beccalli, A. Marchesini, and E. Rossi, Synthesis, 2477 (2001).

  7. D. Pasarella, А. Giardini, М. Martinelli, and А. Silvani, J. Chem. Soc., Perkin Trans. 1, 127 (2001).

  8. I. L. Kotlyarevskii and L. A. Pavlyukhina, Izv. Acad. Nauk SSSR, Ser. Khim., 2363 (1976).

  9. A. P. Terent'ev, M. N. Preobrazhenskaya, and G. M. Sorokina, Zh. Obshch. Khim., 29, 2875 (1959).

    Google Scholar 

  10. E. F. Pratt and T. P. McGovern, J. Org. Chem., 29, 1540 (1964).

    Article  CAS  Google Scholar 

  11. I. L. Kotlyarevskii and L. A. Pavlyukhina, Izv. Akad. Nauk SSSR, Ser. Khim., 1169 (1976).

  12. N. N. Suvorov, A. B. Kamenskii, and Yu. I. Smushkevich, Zh. Org. Khim., 13, 197 (1977).

    CAS  Google Scholar 

  13. A. B. Kamenskii, Thesis for Cand. of Chem. Sci. [in Russian], Moscow (1978).

  14. A. B. Kamenskii, Yu. I. Smushkevich, and N. N. Suvorov, in: Chemistry of Acetylene and its Derivatives. Abstracts of VI All-Union Conference [in Russian], Baku (1979), Part 1, p. 29.

  15. V. P. Gol'mov and N. M. Afanas'ev, Usp. Khim., 27, 785 (1958).

    Google Scholar 

  16. A. P. Kozikowski, М. Okita, М. Kobayashi, and H. G. Floss, J. Org. Chem., 53, 863 (1988).

    Article  CAS  Google Scholar 

  17. C. Wentrup and H. W. Winter, Angew. Chem., 90, 643 (1978).

    Article  CAS  Google Scholar 

  18. D. W. M. Benzies, P. М. Fresneda, R. A. Jones, and M. Hamish, J. Chem. Soc., Perkin Trans. 1, 1651 (1986).

  19. M. S. Shvartsberg, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 4, No. 9, 98 (1983).

    Google Scholar 

  20. M. S. Shvartsberg, A. N. Kozhevnikova, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 466 (1967).

  21. M. S. Shvartsberg, L. N. Bizhan, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1534 (1971).

  22. S. F. Vasilevskii, A. N. Sinyakov, M. S. Shvartsberg, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 690 (1975).

  23. D. E. Ames, D. Bull, and С. А. Takundwa, Synthesis, 364 (1981).

  24. S. J. Havens and P. M. Hergenrother, J. Org. Chem., 50, 1763 (1985).

    Article  CAS  Google Scholar 

  25. W. Zhiyong, L. Wenbin, J. Chao, and G. Qingxiang, Chin. Sci. Bull., 46, 1606 (2001).

    Article  Google Scholar 

  26. T. A. Prikhod’ko, Z. P. Trotsenko, and S. F. Vasilevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1690 (1980).

  27. M. S. Shvartsberg, S. F. Vasilevskii, and T. A. Prikhod’ko, Izv. Akad. Nauk SSSR, Ser. Khim., 2524 (1982).

  28. T. Balle, J. Perregaard, M. T. Ramirez, A. K. Larsen, K. K. Soby, T. Liljefors, and K. Andersen, J. Med. Chem., 46, 265 (2003).

    Article  CAS  Google Scholar 

  29. G. Galambos, Р. Csókási, C. Szántay, Jr., G. Czira, and C. Szántay, Heterocycles, 38, 1459 (1994).

    Article  CAS  Google Scholar 

  30. L. Pérez-Serrano, L. Casarrubios, G. Domingues, P. González-Pérez, and J. Pérez-Castells, Synthesis, 1810 (2002).

  31. N. M. Przhiyalgovskaya, L. I. Kon’kov, D. L. Tarshits, S. V. Salmina, N. T. Segizova, and N. N. Suvorov, 915 (1987). [Chem. Heterocycl. Comp., 23, 751 (1987)].

    Google Scholar 

  32. D. L. Tarshits, S. Yu. Tarasov, and V. N. Buyanov, Izv. Akad. Nauk, Ser. Khim., 2505 (2005).

  33. D. L. Tarshits, N. M. Przhiyalgovskaya, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 1472 (1988). [Chem. Heterocycl. Comp., 24, 1217 (1988)].

    Google Scholar 

  34. M. S. Shvartsberg, A. A. Moroz, and A. N. Kozhevnikova, Izv. Akad. Nauk SSSR, Ser. Khim., 875 (1978).

  35. L. Cassar, J. Organomet. Chem., 93, 253 (1975).

    Article  CAS  Google Scholar 

  36. S. F. Vasilevskii, Thesis for Doctor of Chemical Sciences [in Russian], Novosibirsk (1986).

  37. J. Barluenga, М. Pérez, М. А. Garcia-Martin, and J. M. González, J. Org. Chem., 61, 5804 (1996).

    Article  Google Scholar 

  38. Y. Kondo, S. Kojima, and T. Sakamoto, J. Org. Chem., 62, 6507 (1997).

    Article  CAS  Google Scholar 

  39. Т. Sakakamoto, Т. Nagano, Y. Kondo, and H. Yamanaka, Chem. Pharm. Bull., 36, 2248 (1988).

    Google Scholar 

  40. G. Galambos, C. Szántay, Jr., J. Tamás, and C. Szántay, Jr., Heterocycles, 36, 2241 (1993).

    Article  CAS  Google Scholar 

  41. D. Pasarella, A. Giardini, М. Martinelli, and А. Silvani, J. Chem. Soc., Perkin Trans. 1, 127 (2001).

  42. A. N. Novikov, L. F. Kovaleva, V. P. Lopatinskii, and L. P. Borodulina, Zh. Org. Khim., 13, 665 (1977).

    CAS  Google Scholar 

  43. L. F. Kovaleva, O. I. Reutova, O. A. Sarycheva, O. A. Sheludyakov, A. N. Novikov, and V. D. Filimonov, Zh. Org. Khim., 24, 650 (1988).

    CAS  Google Scholar 

  44. A. Yasuhara, Y. Kanamori, М. Kaneko, А. Numata, Y. Kondo, and Т. Sakomoto, J. Chem. Soc., Perkin Trans. 1, 529 (1999).

  45. J. J. Conde, M. McGuire, and M. Wallace, Tetrahedron Lett., 44, 3081 (2003).

    Article  CAS  Google Scholar 

  46. R. P. Johnson, Сhem. Rev., 89, 1111 (1989).

    Article  CAS  Google Scholar 

  47. D. H. R. Barton and W. D. Ollis (editors), Comprehensive Organic Chemistry [Russian translation], Khimiya, Moscow (1985), Vol. 8, pp. 557, 558.

    Google Scholar 

  48. D. H. R. Barton and W. D. Ollis (editors), General Organic Chemistry [Russian translation], Khimiya, Moscow (1985), Vol. 8, p. 556.

    Google Scholar 

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Authors and Affiliations

  1. Moscow Institute of Open Education, Moscow, 125167, Russia

    D. L. Tarshits

  2. D. I. Mendeleev University of Chemical Technology of Russia, Moscow, 125047, Russia

    N. M. Przhiyalgovskaya & V. N. Buyanov

  3. State Enterprise Scientific-Production Center Pharmzashchita, Federal Agency Medbioekstrem, Khimki, 141400, Moscow Region, Russia

    S. Yu. Tarasov

Authors
  1. D. L. Tarshits
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  2. N. M. Przhiyalgovskaya
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  3. V. N. Buyanov
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  4. S. Yu. Tarasov
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Correspondence to D. L. Tarshits.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 643–670, May, 2009

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Tarshits, D.L., Przhiyalgovskaya, N.M., Buyanov, V.N. et al. Ethynylindoles and their derivatives. Methods of synthesis and chemical transformations (review). Chem Heterocycl Comp 45, 501–523 (2009). https://doi.org/10.1007/s10593-009-0304-9

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