View PDF Version
 
DOI: 10.1039/A705364I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 3581-3586

Pyrolysis of 1-substituted pyrazoles and chloroform at 550 °C: formation of α-carboline from 1-benzylpyrazoles

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

Inayat A. Bhatti, Reginald E. Busby, Murtedza bin Mohamed, John Parrick and C. J. Granville Shaw

Abstract

Pyrolysis of 13CH3 labelled 1-methylpyrazole 8 with chloroform at 550 °C in a continuous flow reactor yields unlabelled 2-chloropyrimidine 9 and 2-cyanopyrrole 10 labelled at the cyano group. However, pyrolysis of 1-benzylpyrazole 14 with chloroform under similar conditions gives 9, 2-phenylpyrimidine 13 and, as the major product, α-carboline 15. Pyrolysis of several substituted 1-(arylmethyl)pyrazoles and the use of 13C and 15N labelled compounds provides direct evidence by which the positions of 7 atoms of 1-benzylpyrazole can be located in the α-carboline. These data support the mechanisms suggested for the formation of 9, 10, and 15.

References

  1. F. De Angelis, A. Gambacorta and R. Nicoletti, Synthesis, 1976, 798 CrossRef CAS .
  2. R. E. Busby, M. Iqbal, J. Parrick and C. J. G. Shaw, J. Chem. Soc., Chem. Commun., 1969, 1344 Search PubMed .
  3. R. E. Busby, M. A. Khan, M. R. Khan, J. Parrick, C. J. G. Shaw and M. Iqbal, J. Chem. Soc., Perkin Trans. 1, 1980, 1427 RSC .
  4. R. E. Busby, L. E. Dorgan, K. I. Lazaar, J. Parrick, S. M. H. Rizvi, C. J. G. Shaw and L. Zor, J. Chem. Technol. Biotechnol., 1985, 35A, 127 CAS .
  5. R. E. Busby, M. A. Khan, M. R. Khan, J. Parrick and C. J. G. Shaw, J. Chem. Soc., Perkin Trans. 1, 1980, 1431 RSC .
  6. C. G. Begg, M. R. Grimmett and P. D. Wethey, Aust. J. Chem., 1973, 26, 2435 CAS .
  7. M. L. White and R. R. Kuntz, Int. J. Chem. Kinet., 1971, 3, 127 CrossRef CAS .
  8. R. E. Busby and L. E. Dorgan, unpublished results .
  9. M. bin Mohamed and J. Parrick, J. Chem. Res., 1980, (S) 43; (M) 577 Search PubMed .
  10. C. Moquin-Pattey and M. Guyot, Tetrahedron, 1989, 45, 3445 CrossRef CAS .
  11. M. bin Mohamed and J. Parrick, Org. Prep. Proc. Int., 1981, 371 CAS .
  12. J. H. Markgraf, D. P. Richardson and R. C. Livingston, Magn. Reson. Chem., 1993, 31, 694 CAS .
  13. R. Huettel and M. E. Schoen, Justus Liebigs Ann. Chem., 1959, 625, 55 CrossRef .
  14. R. G. Jones, J. Am. Chem. Soc., 1949, 71, 3994 CrossRef CAS .
  15. I. I. Grandberg, Khim. Geterosikl. Soedin., 1965, 2, 279 Search PubMed ; Chem. Abstr., 1965, 63, 8339 Search PubMed .
  16. R. Huettel, W. Schwarz, J. Miller and F. Wunsch, Chem. Ber., 1962, 95, 222 CAS .
  17. A. M. Simorov, B. K. Martsokha and F. T. Pozharski, Zh. Obshch. Khim., 1963, 33, 1001 .
  18. R. E. Busby, J. Parrick, S. M. Rizvi and C. J. G. Shaw, J. Chem. Soc., Perkin Trans. 1, 1979, 2786 RSC .
  19. L. Stephenson and W. K. Warburton, J. Chem. Soc. (C), 1970, 1355 RSC .
  20. A. Dorrow and W. Sassenberg, Justus Liebigs Ann. Chem., 1955, 594, 185 .
  21. A. Albert and G. B. Barlin, J. Chem. Soc., 1962, 3129 RSC .
  22. C. A. C. Haley and P. Maitland, J. Chem. Soc., 1951, 3155 RSC .
  23. R. E. Busby, M. Iqbal, M. A. Khan, J. Parrick and C. J. G. Shaw, J. Chem. Soc., Perkin Trans. 1, 1979, 1578 RSC .
Click here to see how this site uses Cookies. View our privacy policy here.