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1-(Trifluoromethyl)-3,4-dihydropyrrolo-[1,2-a] pyrazines: synthesis and reactions with O- and N-nucleophiles

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Chemistry of Heterocyclic Compounds Aims and scope

The method of synthesis has been developed and reactions of 1-(trifluoromethyl)-3,4-dihydro-pyrrolo[1,2-a]pyrazines with O- and N-nucleophiles have been studied. It was found that reactions of nucleophiles with 1-(trifluoro-methyl)pyrrolo[1,2-a]pyrazines transforms the trifluoromethyl group to amide and amidine groups together with aromatization of the pyrrolo[1,2-a]pyrazine system as a result of the formal elimination of a molecule of hydrogen fluoride.

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  1. I. Flament, P. Sonnay, and G. Ohloff, Helv. Chim. Acta, 60, 1872 (1977).

    Article  CAS  Google Scholar 

  2. J. R. Kim and Y. Won, Bull. Korean Chem. Soc., 25, 1874 (2004).

    Article  CAS  Google Scholar 

  3. F. Micheli, B. Bertani, A. Bozzoli, L. Crippa, P. Cavanni, R. Di Fabio, D. Donati, P. Marzorati, G. Merlo, A. Paio, L. Perugini, and P. Zarantonello, Bioorg. Med. Chem. Lett., 18, 1804 (2008).

    Article  CAS  Google Scholar 

  4. Shionogi and Co Limited, US Pat. 6756376 B1 (2004);

  5. E. Wong Ho Fong, L. A. Cortes-Burgos, and B. N. Rogers, Pharmacia and UpJohn Company Limited, WO Pat. 039815 (2004);

  6. A. M. Likhosherstov, V. P. Peresada, V. G. Vinokurov, and A. P. Skoldinov, Zh. Org. Khim., 22, 2610 (1986).

    CAS  Google Scholar 

  7. V. G. Glukhovtsev, Yu. V. Il’in, A. V. Ignatenko and L. Yu. Brezhnev, Izv. Akad. Nauk SSSR Ser. Khim., 2834 (1987).

  8. I. L. Knunyants and G. G. Yakobson (editors), Synthesis of Fluoroorganic Compounds [in Russian], Khimiya, Moscow (1973), p. 312.

    Google Scholar 

  9. V. I. Terenin and A. S. Ivanov, Khim. Geterotsikl. Soedin., 1714 (2007). [Chem. Heterocycl. Comp., 43, 1460 (2007)].

    Google Scholar 

  10. V. I. Terenin and A. S. Ivanov, Khim. Geterotsikl. Soedin., 1267 (2006). [Chem. Heterocycl. Comp., 42, 1101 (2006)].

    Google Scholar 

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Correspondence to V. I. Terenin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1569-1578, October, 2010.

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Terenin, V.I., Galkin, M.V., Kabanova, E.V. et al. 1-(Trifluoromethyl)-3,4-dihydropyrrolo-[1,2-a] pyrazines: synthesis and reactions with O- and N-nucleophiles. Chem Heterocycl Comp 46, 1271–1278 (2011).

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