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A Facile Synthesis of Primary and Secondary Amines

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A facile synthesis of primary amines (R-CH2-NH2, where R = napht-2-yl, anthr-9-yl, phenyl, p-nitrophenyl) and secondary amines (R-NH-R', where R is as mentioned above for primary amines and R'= methyl) is described. The primary amines were obtained by alkylation of di-tert-butyl imidodicarbonate (Boc2NH) under phase-transfer catalysis (PTC) conditions, followed by acidolytic removal of the amine protecting groups. The secondary amines were obtained from the appropriate primary amines by alkylation of their N-tert-butoxycarbonyl derivatives (Boc-NH-R), followed by Boc group acidolysis. It is worth emphasizing that the substrates for synthesis of secondary amines (Boc-NH-R) were obtained via selective removal of one of the tert-butoxycarbonyl groups from the alkylated di-tert-butyl imidodicarbonates (Boc2N-R).
Rocznik
Strony
1067--1072
Opis fizyczny
Bibliogr. 15 poz., rys.
Twórcy
  • Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
autor
  • Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
  • Faculty of Business Administration, Gdynia Maritime University, Morska 83, 81-225 Gdynia, Poland
  • Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
autor
  • Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
Bibliografia
  • 1. Gabriel S., Ber. Dtsch. Chem. Ges., 20, 2224 (1887).
  • 2. Osby J.O., Martin M.G. and Ganem B., Tetrahedron Lett., 25, 2093 (1984).
  • 3. Boyer S.K., Pfund R.A., Portmann R.E., Sedelmeier G.H. and Wetter H.F., Helv. Chim. Acta, 71, 3 (1988).
  • 4. Grehn L. and Ragnarsson U., Synthesis, 275 (1987).
  • 5. Ragnarsson U. and Grehn L., Acc. Chem. Res., 24 (1991).
  • 6. Degerbeck F., Fransson B., Grehn L. and Ragnarsson U., J. Chem. Soc. Perkin Trans I, 245 (1992)
  • 7. Degerbeck F., Fransson B., Grehn L. and Ragnarsson U., J. Chem. Soc. Perkin Trans 1, 11 (1993).
  • 8. Flynn D.L., Zelle R.E. and Grieco P.A., J. Org. Chem., 48, 2424 (1983).
  • 9. Degerbeck F., Grehn L. and Ragnarsson U., Acta Chem. Scan., 47, 896 (1993).
  • 10. Greene T.W. and Wuts P.G.M., Protective Groups in Organic Synthesis, 3rd Ed., A Wiley-Interscience Publications, New York / Toronto, 1999, p. 518.
  • 11. Connell R.D., Helquist P. and Akermark B., J. Org. Chem., 54, 3359(1989).
  • 12. Lakowicz J.R., Principles of Fluorescence Spectroscopy, 2nd Ed., Kluwer Academic / Plenum Publishers New York, 1999.
  • 13. Perrin D.D. and Armarego W.L.F., Purification of Laboratory Chemicals, Pergamon Press, Oxford 1989.
  • 14. Padwa A., Dean D.C., Fairfax D.J. and Xu S.L., J. Org. Chem., 58, 4646 (1993).
  • 15. Tanaka K.-I., Yoshifuji S. and Nitta Y., Chem. Pharm. Bull., 36, 3125 (1988).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0024-0056
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