A Tandem Aminoalkylation of Aldehydes; Application to theSynthesis of Substituted Phenols and Naphthols†

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Mohammad R. Saidi and Hamid R. Khalaji


Abstract

Treatment of a protected salicylic aldehyde (2) and2-hydroxy-1-naphthaldehyde (6) with (trimethylsilyl)dialkylaminesand various nucleophiles in a 5 M diethyl ethersolution of lithium perchlorate gives a variety ofN ,N -dialkylaminophenols (4) and1-(N ,N -dialkylamino)-2-naphthols (8) in shortreaction times and in good yields.


References

  1. K. J. Henry, Jr. and P. A. Grieco, J. Chem. Soc., Chem. Commun., 1993, 510 RSC; P. A. Grieco and E. D. Moher, Tetrahedron Lett., 1993, 34, 5567 CrossRef CAS.
  2. M. R. Saidi, A. Heydari and J. Ipaktschi, Chem. Ber., 1994, 127, 1761 CAS.
  3. M. E. Jung, in Comprehensive Organic Synthesis, ed. B. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 2, p. 893 Search PubMed.
  4. P. Knochel and R. D. Singer, Chem. Rev., 1993, 93, 2117 CrossRef CAS.
  5. A. Devasagayaraj, L. Schwink and P. Knochel, J. Org. Chem., 1995, 60, 3311 CrossRef CAS.
  6. Y. Tamaru, T. Nakamura, M. Salkaguchi, H. Ochiai and Z. Yoshida, J. Chem. Soc., Chem. Commun., 1988, 610 RSC; H. Ochiai, T. Nishihara, Y. Tamaru and Z. Yoshida, J. Org. Chem., 1988, 53, 1343 CrossRef CAS.
  7. J. O. Karlsson, A. Svensson and S. Gronowitz, J. Org. Chem., 1984, 49, 2018 CrossRef CAS.
  8. S. Kobayashi, S. Nagayama and T. Busujima, Tetrahedron Lett., 1996, 37, 9221 CrossRef CAS.
  9. R. D. Smith and H. E. Simmons, Org. Synth., 1973, Coll. Vol. V, 855 Search PubMed.
  10. D. Seebach, C. Bestschuart and M. Schiess, Helv. Chem. Acta., 1984, 67, 1593 Search PubMed.
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