One-pot Synthesis of 1,2,3,4-Tetrafluoroacridines from pentafluorobenzaldehyde1

(Note: The full text of this document is currently only available in the PDF Version )

Adrian J. Adamson, R. Eric Banks, Roy Fields and Anthony E. Tipping


Abstract

1,2,3,4-Tetrafluoroacridines (accompanied in certain cases by their 3-arylamino derivatives) have been prepared in one-pot fashion (via formation in situ of the corresponding Schiff bases) by heating pentafluorobenzaldehyde with a 2 molar equivalence of aniline, para-substituted anilines 4-RC6H4NH2 (R=OMe, Me, But, F, Cl, Br) or 3,5-dimethylaniline in boiling o-dichlorobenzene.


References

  1. Preliminary communication: A. J. Adamson, R. E. Banks and A. E. Tipping, J. Fluorine Chem., 1993, 64, 5 Search PubMed.
  2. P. L. Coe, A. E. Jukes and J. C. Tatlow, J. Chem. Soc. C, 1966, 2020 RSC.
  3. C. M. Jenkins, A. E. Pedler and J. C. Tatlow, Tetrahedron, 1971, 27, 2557 CrossRef CAS.
  4. D. M. Owen, A. E. Pedler and J. C. Tatlow, J. Chem. Soc., Perkin Trans. 1, 1975, 1380 RSC.
  5. T. N. Vasilevskaya, I. I. Baturina, M. I. Kollegova, T. N. Gerasimova and V. A. Barkhash, J. Org. Chem. USSR, 1971, 7, 1269 Search PubMed.
  6. T. N. Gerasimova, L. L. Gelumbovskaya, I. I. Baturina and E. P. Fokin, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1973(part 2), 88(Chem. Abstr., 1973, 79, 53161r) Search PubMed.
  7. T. N. Gerasimova, N. V. Semikolenova and E. P. Fokin, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1977(part 2), 142(Chem. Abstr., 1977, 87, 134160g) Search PubMed.
  8. W. T. Flowers and P. DeFigueredo, unpublished results.
  9. D. J. Bell and W. T. Flowers, unpublished results; D. J. Bell, Ph.D. Thesis, University of Manchester, 1987.
  10. A. J. Adamson, Y. Archambeau, R. E. Banks, B. Beagley, M. Helliwell, R. G. Pritchard and A. E. Tipping, Acta Crystallogr., Sect. C, 1994, 50, 967 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.