Skip to main content
Log in

Syntheses based onβ-phenylethylamines. I. Preparation of substitutedβ-phenylethylamines

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

A comparative study has been made of methods of synthesizing substituted β-phenylethylamines via the corresponding nitriles and via nitrostyrenes, and a superiority of the latter method has been established. The possibility has been shown for the first time of reducing nitrostyrenes to saturated amines with diisobutylaluminum hydride (DIBAH). The use of DIBAH as reducing agent enables amines to be obtained in high yields.

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.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. K. M. Dyumaev and I. S. Belostotskii,Zh. Obshch. Khim. 32, 2661 (1962).

    Google Scholar 

  2. M. Shamma,The Isoquinoline Alkaloids, Academic Press, New York (1972); K. W. Bentley, Nat. Prod. Rep.,2, 81 (1985).

    Google Scholar 

  3. M. V. Rubtsov and A. G. Baichikov,Synthetic Pharmaceutical Chemicals [in Russian], Meditsina, Moscow (1971).

    Google Scholar 

  4. T. Kametani, K. Fukumoto, S. Shibuya, H. Nemoto, T. Nakano, T. Sughara, T. Takahashi, and Y. Aizowa,J. Chem. Soc. Perkin 1, 1435 (1972).

    Google Scholar 

  5. C. A. Buehler and D. E. Pearson,Survey of Organic Syntheses, Interscience, New York, Vol. I (1970), p. 202.

    Google Scholar 

  6. E. Wintefeldt,Synthesis, 617 (1975).

  7. G. K. Tusupbekova and I. V. Kirilyus,Khim.-farm. Zh., 204 (1985).

  8. C. B. Gairand and G. R. Lappin,J. Org. Chem.,18, 1 (1953).

    Google Scholar 

  9. W. J. Gensler and C. M. Samour,J. Am. Chem. Soc. 73, 5555 (1951).

    Google Scholar 

  10. M. Erne and F. Ramirez,Helv. Chim. Acta 33, 912 (1950); Y. Inubushi and K. Fujitani, J. Pharm. Soc. Jpn.,78, 486 (1958);Chem. Abstr. 52, 17273f (1958).

    Google Scholar 

  11. F. Ramierez and A. Burger,J. Am. Chem. Soc. 72, 2781 (1950).

    Google Scholar 

  12. R. Grewe, E. Nolte, and R.-H. Rotzoll,Chem. Ber. 89, 600 (1956).

    Google Scholar 

  13. J. R. Butterich and A. M. Unrau,J. Chem. Soc., Chem. Commun., 307 (1974).

  14. J. R. Sheth and O. N. Tolkachev,Indian J. Appl. Chem. 31, 137 (1968).

    Google Scholar 

  15. H. L. Curtis, US Patent No. 3,187,046 (1965);Chem. Abstr. 63, 9868d (1965); G. Stochdorph and O. V. Schickh, US Patent No. 848,197 (1952);Chem. Abstr. 47, 4538b (1952).

  16. J. Finkelstein,J. Am. Chem. Soc. 73, 550 (1951).

    Google Scholar 

  17. A. Brossi, F. Schenker, R. Schmidt, R. Banziger, and H. Neimgruber,Helv. Chim. Acta,49, 403 (1966).

    Google Scholar 

  18. T. Toshio, N. Kenryo, and S. Shuichi,Chem. Pharm. Bull. 19, 817 (1971).

    Google Scholar 

  19. B. Staskun and T. Es,J. Chem. Soc., 531 (1966).

  20. W. A. Lazier and H.R. Arnold,Org. Synth., Coll. Vol. II, 142 (1943).

    Google Scholar 

  21. M. A. Schwartz, M. Zoda, B. Vishnuvajjala, and I. Mami,J. Org. Chem. 41, 2502 (1976).

    Google Scholar 

Download references

Authors

Additional information

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 67–74, January–February, 1990.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vinogradova, V.I., Yunusov, M.S., Kuchin, A.V. et al. Syntheses based onβ-phenylethylamines. I. Preparation of substitutedβ-phenylethylamines. Chem Nat Compd 26, 54–59 (1990). https://doi.org/10.1007/BF00605201

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00605201

Keywords

Navigation