Skip to main content
Log in

Synthesis of 6,7-Dimethoxy-1,3,4,8b-Tetrahydroazirino [2,1-a]Isoquinoline-N-Borane and bis-(6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline)-1,1′-Ene

  • Published:
Chemistry of Natural Compounds Aims and scope

Homoveratrylamine was condensed with glycolic and oxalic acids in order to synthesize the corresponding amides. Their behavior in the Bischler—Napieralski reaction was studied. The structures of resulting tetrahydroisoquinolines 7 and 9 were confirmed using IR and NMR spectral data and x-ray crystal structures.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. M. Shamma, The Isoquinoline Alkaloids. Chemistry and Pharmacology, Vol. 25, Academic Press, New York, London, 1972.

    Google Scholar 

  2. M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 64, 1249 (2001).

    Article  CAS  PubMed  Google Scholar 

  3. R. Suau, N. Posadas, M. V. Silva, and M. Valpuesta, Phytochemistry, 49, 2551 (1998).

    Article  CAS  Google Scholar 

  4. T. S. Kaufman, J. Chem. Soc. Perkin Trans. 1, 2497 (1996).

    Article  Google Scholar 

  5. E. P. White, N. Z. J. Sci. Technol., Sect. B, 25, 152 (1944).

  6. G. L. Gupta, Planta Med., 19, 55 (1971).

    CAS  Google Scholar 

  7. A. R. Battersby and T. P. Edwards, J. Chem. Soc., 1214 (1960).

  8. F. Benington and R. D. Morin, J. Org. Chem., 26, 194 (1961).

    Article  Google Scholar 

  9. Z. Czarnocki, D. B. MacLean, and W. A. Szarek, J. Chem. Soc. Chem. Commun., 1318 (1985); Can. J. Chem., 64, 2206 (1986).

  10. T. S. Kaufman, Synth. Commun., 23, No. 4, 473 (1993).

    Article  CAS  Google Scholar 

  11. I. Guben, Methods of Organic Chemistry [in Russian], Vol. 3, No. 1, Goskhimtekhizdat, Moscow-Leningrad, 1934, p. 71.

    Google Scholar 

  12. R. Suau, I. Ruiz, N. Posadas, and M. Valpuesta, Heterocycles, 43, 545 (1996).

    Article  CAS  Google Scholar 

  13. D. J. Brooks, D. S. Dowell, D. E. Minter, and M. C. Villerreal, J. Org. Chem., 49, 130 (1984).

    Article  CAS  Google Scholar 

  14. E. Vedejs, A. S. B. Prasad, J. T. Kendall, and J. S. Russel, Tetrahedron, 59, 9849 (2003).

    Article  CAS  Google Scholar 

  15. J. M. Concellon, J. R. Suarez, S. Garcia-Granda, and M. R. Diaz, Angew. Chem., Int. Ed., 43, 4333 (2004).

    Article  CAS  Google Scholar 

  16. B. K. H. Chan, B. Deng, M. W. Jones, and R. W. Read, Tetrahedron, 62, 4979 (2006); M. A. Siegfried, H. Hilpert, M. Rey, and A. S. Dreiding, Helv. Chim. Acta, 63, 938 (1980).

  17. S. Saidov, E. Yu. Mazur, K. K. Turgunov, B. Tashkhodzhaev, M. G. Levkovich, and V. I. Vinogradova, Chem. Nat. Compd., 50, 503 (2014).

    Article  CAS  Google Scholar 

  18. G. M. Sheldrick, Program for Empirical Absorption Correction of Area Detector Data, University of Goettingen, Goettingen, 1996.

    Google Scholar 

  19. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Sh. Saidov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2014, pp. 771–774.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Saidov, A.S., Turgunov, K.K., Tashkhodzhaev, B. et al. Synthesis of 6,7-Dimethoxy-1,3,4,8b-Tetrahydroazirino [2,1-a]Isoquinoline-N-Borane and bis-(6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline)-1,1′-Ene. Chem Nat Compd 50, 892–896 (2014). https://doi.org/10.1007/s10600-014-1108-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-014-1108-4

Keywords

Navigation