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Synthesis of 4-phenyl-1-(2-thienyl)-2,3,4,9-tetrahydro-1H-β-carboline

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Abstract

The Pictet-Spengler reaction involving β-phenyltryptamine was shown to be diastereo-specific with formation primarily of the (1S*,4R*) diastereomer of 4-phenyl-1-(2-thienyl)-2,3,4,9-tetrahydro-1H-β-carboline, a compound with potential GABA-receptor activity.

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References

  1. H. R. Dodd, C. Ovannes, G. Robert, and P. Potier, J. Med. Chem., 32, 1272 (1989).

    Article  PubMed  CAS  Google Scholar 

  2. S. Srivastava, A. Agarwal, P. Chauhan, S. Agarwal, A. Bhaduri, S. Singh, N. Fatima, and R. Chatterjee, J. Med. Chem., 42, 1667 (1999).

    Article  PubMed  CAS  Google Scholar 

  3. S. Srivastava, A. Agarwal, P. Chauhan, S. Agarwal, A. Bhaduri, S. Singh, N. Fatima, and R. Chatterjee, Bioorg. Med. Chem., 7, 1223 (1999).

    Article  PubMed  CAS  Google Scholar 

  4. H. J. Zhu, B. T. Zhao, G. Y. Zuo, C. U. Pittman, W. M. Daic, and X. J. Hao, Tetrahedron: Asymmetry, 12, 2613 (2001).

    Article  CAS  Google Scholar 

  5. C.-Y. Wu and C.-M. Sun, Synlett, 10, 1709 (2002).

    Google Scholar 

  6. W.-B. Yeh, M.-J. Lin, and C.-M. Sun, Tetrahedron Lett., 44, 4923 (2003).

    Article  CAS  Google Scholar 

  7. B. B. Semenov, K. A. Novikov, A. N. Spitsin, V. N. Azev, and V. V. Kachala, Khim. Prir. Soedin., 481 (2004).

  8. B. B. Semenov, K. A. Novikov, V. V. Kachala, V. N. Azev, and Yu. I. Smushkevich, Izv. Vyssh. Uchebn. Zaved., Ser. Khim., 5, 149 (2005).

    Google Scholar 

  9. B. B. Semenov, K. A. Novikov, V. N. Azev, and V. V. Kachala, Izv. Akad. Nauk, Ser. Khim., 4, 964 (2005).

    Google Scholar 

  10. B. B. Semenov, K. A. Novikov, V. N. Azev, and V. V. Kachala, Khim. Geterotsikl. Soedin., 10, 1521 (2005).

    Google Scholar 

  11. B. B. Semenov, K. A. Novikov, V. V. Kachala, V. N. Azev, V. I. Goncharov, and I. V. Aksenova, Ves. Stavr. Gos. Univ., 38, 5 (2005).

    Google Scholar 

  12. K. Beelitz, G. Buchholz, and K. Praefcke, Liebigs Ann. Chem., 12, 2043 (1979).

    Google Scholar 

  13. A. Pictet and T. Spengler, Ber., 44, 2030 (1911).

    CAS  Google Scholar 

  14. J. Lehmann, N. Jiang, and A. Behncke, Arch. Pharm., 326, 813 (1993).

    Article  CAS  Google Scholar 

  15. B. E. Maryanoff, D. F. McComsey, and B. A. Duhl-Emswiler, J. Org. Chem., 48, 5062 (1983).

    Article  CAS  Google Scholar 

  16. R. Adams, ed., Organic Reactions, Vol. 6, John Wiley and Sons Inc., New York (1951).

    Google Scholar 

  17. E. D. Cox and J. M. Cook, Chem. Rev., 95, 1797 (1995).

    Article  CAS  Google Scholar 

  18. T. Hino and M. Nakagawa, Heterocycles, 46, 673 (1997).

    Article  CAS  Google Scholar 

  19. E. P. Styngach, K. I. Kuchkova, and T. M. Efremova, Khim. Geterotsikl. Soedin., 1523 (1973).

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 468–470, September–October, 2006.

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Semenov, B.B., Novikov, K.A., Kachala, V.V. et al. Synthesis of 4-phenyl-1-(2-thienyl)-2,3,4,9-tetrahydro-1H-β-carboline. Chem Nat Compd 42, 582–584 (2006). https://doi.org/10.1007/s10600-006-0218-z

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  • DOI: https://doi.org/10.1007/s10600-006-0218-z

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