View PDF Version
 
DOI: 10.1039/A701103B (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2229-2236

Approaches to 1,1-disubstituted cinnolin-3-ylio oxides: synthesis and reactivity of a new class of heterocyclic betaines

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

Vicente J. Arán, Juan L. Asensio, José Molina, Pilar Muñoz, José R. Ruiz and Manfred Stud

Abstract

The cinnolin-3-ylio oxides 6, a new class of heterocyclic aminimide, can be prepared by intramolecular cyclization of the N[hair space]′,N[hair space]′-disubstituted (2-fluorophenyl)acetohydrazides 5. Attempts to prepare these betaines by an alternative route, namely cyclization of the nitrenes expected from the thermal decomposition of (2-dialkylaminophenyl)acetyl azides 11, failed, Curtius rearrangement-derived compounds being the main products isolated from these processes. Hydrochlorides of the cinnolin-3-ylio oxides 6 undergo alkyl halide elimination to yield the 1-(ω-chloroalkyl)cinnolin-3-ols 19a,b or 1-methylcinnolin-3-ol 21. Oxidation of the latter to the 3-hydroxycinnolin-4-one 22, its methylation to the corresponding N[hair space]1,O- 23 and N[hair space]1,N[hair space]2-dimethyl 24 derivatives as well as the cyclization of 1-(5-chloropentyl)cinnolin-3-ol 19a to the diazepino[1,2-a]cinnolinone 20 are also reported.

References

  1. R. W. Jemison, S. Mageswaran, W. D. Ollis, S. E. Potter, A. J. Pretty, I. O. Sutherland and Y. Thebtaranonth, J. Chem. Soc., Chem. Commun., 1970, 1201 RSC; R. W. Jemison, S. Mageswaran, W. D. Ollis, I. O. Sutherland and Y. Thebtaranonth, J. Chem. Soc., Perkin Trans. 1, 1981, 1154 RSC.
  2. W. J. McKillip, E. A. Sedor, B. M. Culbertson and S. Wawzonek, Chem. Rev., 1973, 73, 255 CrossRef CAS.
  3. J. R. Ruiz, V. J. Arán, J. L. Asensio, M. Flores and M. Stud, Liebigs Ann. Chem., 1994, 679 Search PubMed.
  4. J. R. Ruiz, V. J. Arán and M. Stud, Tetrahedron Lett., 1988, 29, 697 CrossRef CAS.
  5. V. J. Arán, J. L. Asensio, J. R. Ruiz and M. Stud, J. Chem. Res., 1993, (S), 218; (M), 1322 Search PubMed.
  6. N. M. Waldron, M. Montevalli, S. Azam and P. C. Dasopoulos, J. Chem. Soc., Chem. Commun., 1995, 81 RSC.
  7. N. M. Waldron and M. Raza, J. Chem. Soc., Perkin Trans. 1, 1996, 271 RSC.
  8. J. Martin, O. Meth-Cohn and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 1974, 2451 RSC.
  9. V. J. Arán, J. L. Asensio, J. R. Ruiz and M. Stud, J. Chem. Soc., Perkin Trans. 1, 1993, 1119 RSC.
  10. V. J. Arán, M. Flores, P. Muñoz, J. R. Ruiz, P. Sánchez-Verdú and M. Stud, Liebigs Ann., 1995, 817 CAS.
  11. J. F. Bunnett and R. E. Zahler, Chem. Rev., 1951, 49, 273 CrossRef CAS.
  12. W. Walter and K. J. Reubke, Chem. Ber., 1970, 103, 2197 CAS.
  13. U. Anthoni, C. Larsen and P. H. Nielsen, Acta Chem. Scand., 1969, 23, 3513 CAS.
  14. M. J. S. Dewar and W. B. Jennings, J. Am. Chem. Soc., 1973, 95, 1562 CrossRef CAS.
  15. A. F. Cameron, N. J. Hair, D. G. Morris and D. M. Hawley, J. Chem. Soc., Chem. Commun., 1971, 725 RSC.
  16. Lilly Industries Ltd., BP 1 299 171/ 1972(Chem. Abstr., 1973, 78, P97509u) Search PubMed.
  17. P. A. S. Smith, Org. React., 1946, 3, 337.
  18. L. Baiocchi, G. Corsi and G. Palazzo, Synthesis, 1978, 633 CrossRef CAS.
  19. V. J. Arán, M. Flores, P. Muñoz, J. A. Páez, P. Sánchez-Verdú and M. Stud, Liebigs Ann., 1996, 683 CAS.
  20. K. Sindelar, J. Holubek, A. Dlabak, M. Bartosova and M. Protiva, Collect. Czech. Chem. Commun., 1977, 42, 2231 CAS.
  21. L. A. Carpino, J. Am. Chem. Soc., 1957, 79, 4427 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.