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The First Example of 4,7,8,9-Tetrahydrothieno-[2,3-d]Azocine Synthesis by Domino Reaction of 4-ARYL-4,5,6,7-Tetrahydrothieno[3,2-c]Pyridines with Activated Alkynes

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Chemistry of Heterocyclic Compounds Aims and scope

1-Aryl-substituted tetrahydrothieno[3,2-с]pyridines easily undergo domino reactions with activated alkynes, giving good yields of the corresponding tetrahydrothieno[2,3-d]azocines. The reactions of 1-methyl-substituted tetrahydrothieno[3,2-с]pyridine were more complicated.

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References

  1. J. Bosch, D. Mauleon, F. Boncompte, and R. Ganados, J. Heterocycl. Chem., 18, 263 (1981).

    Article  CAS  Google Scholar 

  2. J. W. H. Watthey, T. Gavin, and M. Dasai, J. Med. Chem., 27, 816 (1984).

    Article  CAS  Google Scholar 

  3. Y. Ishihara, K. Hirai, M. Miyamoto, and G. Goto, J. Med. Chem., 37, 2292 (1994).

    Article  CAS  Google Scholar 

  4. A. A. Carotti, M. de Candia, M. Catto, T. N. Borisova, A. V. Varlamov, E. Méndez-Álvarez, R. Soto-Otero, and L. G. Voskressensky, and C. Altomare, Bioorg. Med. Chem., 14, 7205 (2006).

    Article  CAS  Google Scholar 

  5. L. G. Voskressensky, L. N. Kulikova, T. N. Borisova, and A. V. Varlamov, Adv. Heterocycl. Chem., 96, 81 (2008).

    Article  CAS  Google Scholar 

  6. E. D. Thorsett, E. E. Harris, S. D. Aster, E. R. Peterson, J. P. Snyder, J. P. Springer, J. Hirshfield, E. W. Tristram, A. A. Patchett, E. H. Ulm, and T. C. Vassil, J. Med. Chem., 29, 251 (1986).

    Article  CAS  Google Scholar 

  7. V. N. Mutafova-Yambolieva, and K. D. Keef, Eur. J. Pharmacol., 411, 123 (2001).

    Article  CAS  Google Scholar 

  8. A. B. Malmberg, L. R. Hedley, J. R. Jasper, J. C. Hunter, and A. I. Basbaum, Br. J. Pharmacol., 132, 1827 (2001).

    Article  CAS  Google Scholar 

  9. M. Xian, X. Li, X. Tang, X. Chen, Z. Zheng, J. J. Galligan, D. L. Kreulen, and P. G. Wang, Bioorg. Med. Chem. Lett., 11, 2377 (2001).

    Article  CAS  Google Scholar 

  10. L. G. Voskressensky, S. A. Kovaleva, T. N. Borisova, A. V. Listratova, A. B. Eresko, V. S. Tolkunov, S. V. Tolkunov, and A. V. Varlamov, Tetrahedron, 66, 9421 (2010).

    Article  CAS  Google Scholar 

  11. L. G. Voskressensky, A. A. Titov, T. N. Borisova, A. V. Listratova, R. S. Borisov, L. N. Kulikova, and A. V. Varlamov, Tetrahedron, 66, 5140 (2010).

    Article  CAS  Google Scholar 

  12. L. G. Voskressensky, T. N. Borisova, A. V. Listratova, Е. А. Sorokina, S. V. Tolkunov, and A. V. Varlamov, Russ. Chem. Bull., 54, 1041 (2007). [Izv. Akad. Nauk, Ser. Khim., 1003 (2007).]

    Article  Google Scholar 

  13. L. G. Voskressensky, T. N. Borisova, S. A. Kovaleva, L. N. Kulikova, A. V. Listratova, S. V. Tolkunov, and A. V. Varlamov, Chem. Heterocycl. Compd., 46, 354 (2010). [Khim. Geterotsikl. Soedin., 447 (2010).]

    Article  CAS  Google Scholar 

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Correspondence to L. G. Voskressensky.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1451-1458, September, 2014.

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Voskressensky, L.G., Borisova, T.N., Chervyakova, T.M. et al. The First Example of 4,7,8,9-Tetrahydrothieno-[2,3-d]Azocine Synthesis by Domino Reaction of 4-ARYL-4,5,6,7-Tetrahydrothieno[3,2-c]Pyridines with Activated Alkynes. Chem Heterocycl Comp 50, 1338–1345 (2014). https://doi.org/10.1007/s10593-014-1597-x

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