Spiro-fused Tricyclic 7,8,9,10-Tetrahydro-3H,5H-benzo[d]pyrrolo[1,2-c][1,2,3]triazoles and their Thermal Rearrangement to 1,3,4-Trisubstituted 2-(4-Cyanobutyl)pyrroles. Azolium 1,3-Dipoles†

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

Richard N. Butler and Denise C. Grogan


Abstract

New substituted tricyclic 7,8,9,10-tetrahydro-3H-5,H-benzo[d]pyrrolo[1,2-c][1,2,3]triazoles 4 and 5 rearrange on heating to afford high yields of 1-arylamino-2-(4-cyanobutyl)-3,4-bis(alkoxycarbonyl)pyrroles 6 and 7.


References

  1. R. J. Sundberg, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. Scriven, Pergamon, Oxford, 1996, vol. 2, pp. 119–206 and references cited therein Search PubMed.
  2. N. P. Pavri and M. L. Trudell, J. Org. Chem., 1997, 62, 2649 Search PubMed.
  3. D. M. Collard and M. A. Fox, J. Am. Chem. Soc., 1991, 113, 9415 Search PubMed; C. P. Andrieux, P. Audebert, P. Hapiot and J. M. Saveant, J. Am. Chem. Soc., 1990, 112, 2439 Search PubMed.
  4. R. N. Butler, P. D. McDonald, P. McArdle and D. Cunningham, J. Chem. Soc., Perkin Trans. 1, 1996, 1617 Search PubMed.
  5. E. Vedejs, S. Larsen and F. G. West, J. Org. Chem., 1985, 50, 2170 Search PubMed.
  6. R. C. F. Jones, J. R. Nichols and M. T. Cox, Tetrahedron Lett., 1990, 31, 2333 Search PubMed.
  7. W. von Philipsoborn and R. Muller, Angew. Chem., Int. Ed. Engl., 198, 25, 383 Search PubMed.
  8. R. N. Butler, J. P. Duffy, D. Cunningham, P. McArdle and L. A. Burke, J. Chem. Soc., Perkin Trans. 1, 1992, 147 Search PubMed.
  9. R. N. Butler, F. A. Lysaght, P. D. McDonald, C. S. Pyne, P. McArdle and D. Cunningham, J. Chem. Soc., Perkin Trans. 1, 1996, 1623 Search PubMed; R. N. Butler, A. M. Gillan, S. Collier and J. P. James, J. Chem. Res. (S), 1987, 332 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.