A new route to medium and large heterocyclic compounds

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

Tina Ventrice, Eva M. Campi, W. Roy Jackson and Antonio F. Patti


Abstract

Hydrogenation of nitrobenzenes bearing aldehyde-containing substituents over heterogeneous platinum or palladium catalysts gives medium and/or large heterocyclic amines as a result of simple or dimeric cyclisation in moderate to good yields; a range of heteroatoms can be incorporated into the macrocycles, enhancing their potential as ligands.


References

  1. P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, London, 1979, p. 132 Search PubMed.
  2. H. Ina, M. Ito and C. Kibayashi, J. Org. Chem., 1996, 61, 1023 CrossRef CAS.
  3. E. M. Campi, W. R. Jackson and A. E. Trnacek, Aust. J. Chem., 1997, 50, 807 CAS; D. Anastasiou, E. M. Campi, H. Chaouk and W. R. Jackson, Tetrahedron, 1992, 48, 7467 CrossRef CAS.
  4. A. L. J. Beckwith and W. B. Gara, J. Chem. Soc., Perkin Trans. 2, 1975, 593 RSC; L. Garanti and G. Zecchi, J. Heterocycl. Chem., 1993, 30, 559 CAS; G. Broggini, L. Garanti, G. Molteni and G. Zecchi, Tetrahedron, 1997, 53, 3005 CrossRef CAS.
  5. G. D. Cuny and S. L. Buchwald, J. Am. Chem. Soc., 1993, 115, 2066 CrossRef; I. Ojima, D. M. Iula and M. Tzamarioudaki, Tetrahedron Lett., 1998, 39, 4599 CrossRef CAS.
  6. C. Botteghi, R. Ganzerla, M. Lenarda and G. Moretti, J. Mol. Catal., 1987, 40, 129 CrossRef CAS; I. Amer and H. Alper, J. Am. Chem. Soc., 1990, 112, 3674 CrossRef CAS.
  7. Insight II (v 4.0.0)(Discover) Molecular Modelling System; Molecular Simulations Inc., 9685 Scranton Road, San Diego, CA 92121-3752 (USA).
  8. A. J. Leong, L. F. Lindoy, D. C. R. Hockless, G. F. Swiegers and S. B. Wild, Inorg. Chim. Acta, 1996, 246, 371 CrossRef.
  9. D. Parker and J. A. G. Williams, J. Chem. Soc., Perkin Trans. 2, 1995, 1305 RSC.
  10. J. J. Christensen, D. J. Eatough and R. M. Izatt, Chem. Rev., 1974, 74, 351 CrossRef; R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 1992, 92, 1261 CrossRef CAS.
  11. A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97, 1515 CrossRef.
  12. E. Ishow, A. Credi, V. Balzani, F. Spadola and L. Mandolini, Chem. Eur. J., 1999, 5, 984 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.