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Synthesis of Epoxyisoindolo[1,2-a]isoquinolinium Salts by an Intramolecular [2+4] Cycloaddition Reaction in 2-Allyl-1-furylisoquinolinium Halides

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Chemistry of Heterocyclic Compounds Aims and scope

We examined the tandem alkylation/[2+4] cycloaddition of 1-(2-furyl)-3,4-dihydroisoquinolines by various allyl halides. It was found that the process occurred through the intermediate formation of 2-allyl-1-furyl-3,4-dihydroisoquinolinium salts with a subsequent intramolecular exo addition of the allyl fragment to the furan ring. The adducts obtained were structural analogs of the isoindolo-[1,2-a]isoquinoline alkaloids jamtine and hirsutine.

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References

  1. G. Manikumar and M. Shamma, Heterocycles, 14, 827 (1980).

    Article  CAS  Google Scholar 

  2. R. Alonso, L. Castedo, and D. Domínguez, Tetrahedron Lett., 26, 2925 (1985).

    Article  CAS  Google Scholar 

  3. V. U. Ahmad, A. Rahman, T. Rasheed, and H. Rehman, Heterocycles, 26, 1251 (1987).

    Article  CAS  Google Scholar 

  4. V. U. Ahmad and S. Iqbal, Phytochemistry, 33, 735 (1993).

    Article  Google Scholar 

  5. V. U. Ahmad and S. Iqbal, Nat. Prod. Lett., 2, 105 (1993).

    Article  CAS  Google Scholar 

  6. T. Rasheed, M. N. I. Khan, S. S. A. Zhadi, and S. Durrani, J. Nat. Prod., 54, 582 (1991).

    Article  CAS  Google Scholar 

  7. R. Grigg, V. Sridharan, P. Stevenson, S. Sukirthalingam, and T. Worakun, Tetrahedron, 46, 4003 (1990).

    Article  CAS  Google Scholar 

  8. R. Grigg, V. Sridharan, P. Stevenson, and T. Worakun, J. Chem. Soc., Chem. Commun., 23, 1697 (1986).

    Article  Google Scholar 

  9. Y. Abe, A. Ohsawa, and H. Igeta, Heterocycles, 19, 49 (1982).

    Article  CAS  Google Scholar 

  10. H. Heaney and K. F. Shuhaibar, Tetrahedron Lett., 35, 2751 (1994).

    Article  CAS  Google Scholar 

  11. T. V. Alpatova and V. G. Yashunskii, Khim. Geterotsikl. Soedin., 1084 (1981). [Chem. Heterocycl. Compd., 17, 804 (1981)].

    Google Scholar 

  12. E. Sobarzo-Sánchez, E. Uriarte, L. Santana, R. A. Tapia, and P. P. Lourido, Helv. Chim. Acta, 93, 1385 (2010).

    Article  Google Scholar 

  13. Y. Tominaga, Y. Shiroshita, Y. Matsuda, and A. Hosomi, Heterocycles, 26, 2073 (1987).

    Article  CAS  Google Scholar 

  14. N. S. Basketter and A. O. Plunkett, J. Chem. Soc., Chem. Commun., 188b (1973).

  15. Y. Tang, J. C. Fettinger and J. T. Shaw, Org. Lett., 11, 3802 (2009).

    Article  CAS  Google Scholar 

  16. J. Pérard-Viret, F. Souquet, M.-L. Manisse, and J. Royer, Tetrahedron Lett., 51, 96 (2010).

    Article  Google Scholar 

  17. M. Winn and H. E. Zaugg, J. Org. Chem., 33, 3779 (1968).

    Article  CAS  Google Scholar 

  18. G. J. Hitchings, M. Helliwell, and J. M. Vernon, J. Chem. Soc., Perkin Trans. 1, 83 (1990).

  19. M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 871 (1996).

  20. A. R. Katritzky, S. Mehta, and H.-Y. He, J. Org. Chem., 66, 148 (2001).

    Article  CAS  Google Scholar 

  21. M. I. Collado, I. Manteca, N. Sotomayor, M.-J. Villa, and E. Lete, J. Org. Chem., 62, 2080 (1997).

    Article  CAS  Google Scholar 

  22. I. González-Temprano, I. Osante, E. Lete, and N. Sotomayor, J. Org. Chem., 69, 3875 (2004).

    Article  Google Scholar 

  23. J. Selvakumar and C. R. Ramanathan, Org. Biomol. Chem., 9, 7643 (2011).

    Article  CAS  Google Scholar 

  24. G. Kim, J. H. Kim, W.-J. Kim, and Y. A. Kim, Tetrahedron Lett., 44, 8207 (2003).

    Article  CAS  Google Scholar 

  25. P. L. Barili and V. Scartoni, J. Heterocycl. Chem., 22, 1199 (1985).

    Article  CAS  Google Scholar 

  26. R. B. Othman, R. Affani, M.-J. Tranchant, S. Antoniotti, V. Dalla, and E. Duñach, Angew. Chem., Int. Ed., 49, 776 (2010).

    Article  Google Scholar 

  27. A. Moreau, A. Couture, E. Deniau, P. Grandclaudon, and S. Lebrun, Tetrahedron, 60, 6169 (2004).

    Article  CAS  Google Scholar 

  28. F. I. Zubkov, J. D. Ershova, A. A. Orlova, V. P. Zaytsev, E. V. Nikitina, A. S. Peregudov, A. V. Gurbanov, R. S. Borisov, V. N. Khrustalev, A. M. Maharramov, and A. V. Varlamov, Tetrahedron, 65, 3789 (2009).

    Article  CAS  Google Scholar 

  29. F. I. Zubkov, J. D. Ershova, V. P. Zaytsev, M. D. Obushak, V. S. Matiychuk, E. A. Sokolova, V. N. Khrustalev, and A. V. Varlamov, Tetrahedron Lett., 51, 6822 (2010).

    Article  CAS  Google Scholar 

  30. K. T. Tagmazyan, G. O. Torosyan, R. S. Mkrtchan, and A. T. Babayan, Arm. Khim. Zh., 29, 352 (1976); Chem. Abstr., 86, 42746 (1977).

    Google Scholar 

  31. A. T. Babayan, K. T. Tagmazyan, and R. S. Mkrtchan, Dokl. Akad. Nauk Arm. SSR, Org. Khim., 55, 224 (1972); Chem. Abstr., 79, 92058 (1973).

    Google Scholar 

  32. K. T. Tagmazyan, R. S. Mkrtchan, and A. T. Babayan, Arm. Khim. Zh., 27, 957 (1974); Chem. Abstr., 82, 111234 (1975).

    Google Scholar 

  33. J. Sauer, Angew. Chem., Int. Ed., 6, 16 (1967).

    Article  CAS  Google Scholar 

  34. F. A. A. Toze, J. D. Ershova, M. D. Obushak, F. I. Zubkov, and V. N. Khrustalev, Acta Crystallogr., Е66, o1388 (2010).

    Google Scholar 

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Authors and Affiliations

  1. Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    F. I. Zubkov, V. P. Zaytsev, Yu. D. Ershova, D. F. Mertsalov, E. A. Sorokina, E. V. Nikitina & A. V. Varlamov

  2. Ivan Franko Lviv National University, 6 Kyril and Mefody St., Lviv, 79005, Ukraine

    M. D. Obushak, Yu. I. Gorak & R. Z. Lytvyn

Authors
  1. F. I. Zubkov
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  2. V. P. Zaytsev
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  3. M. D. Obushak
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  4. Yu. D. Ershova
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  5. D. F. Mertsalov
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  6. E. A. Sorokina
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  7. E. V. Nikitina
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  8. Yu. I. Gorak
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  9. R. Z. Lytvyn
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  10. A. V. Varlamov
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Corresponding author

Correspondence to V. P. Zaytsev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 798–812, May, 2013.

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Zubkov, F.I., Zaytsev, V.P., Obushak, M.D. et al. Synthesis of Epoxyisoindolo[1,2-a]isoquinolinium Salts by an Intramolecular [2+4] Cycloaddition Reaction in 2-Allyl-1-furylisoquinolinium Halides. Chem Heterocycl Comp 49, 746–759 (2013). https://doi.org/10.1007/s10593-013-1306-1

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  • DOI: https://doi.org/10.1007/s10593-013-1306-1

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