Abstract
Optically active camphordihydro-2,3-pyrazine and camphorquinoxaline were prepared from camphoroquinone enantiomers. It was shown that (1S,4R)-(+)-camphoroquinone was formed by oxidation of (1S,3R, 4R)-(−)-3-bromocamphor and (1R,4S)-(−)-camphoroquinone from (1R,3S, 4S)-(+)-3-bromocamphor, respectively. Camphor anhydride was a side product (6–10%) of the reaction.
Similar content being viewed by others
References
W. Oppolzer, C. Chapuis, D. Dupuis, and M. Guo, Helv. Chim. Acta, 68, 2100 (1985).
H. Herzog and H. D. Scharf, Synthesis, 788 (1986).
R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 32,50, 7373 (1991).
J. D. White, D. J. Wardrop, and K. F. Sundermann, Org. Synth., 79, 125 (2002).
D. Lucet, T. Le Gall, and C. Mioskowski, Angew. Chem., Int. Ed. Engl., 37, 2580 (1998).
Y. L. Bennani and S. Hanessian, Chem. Rev., 97, 3161 (1997).
A. Togni and L. M. Venanzi, Angew. Chem., Int. Ed. Engl., 33, 497 (1994).
K. Tomioka, Synthesis, 541 (1990).
C. H. Heathcock and S. C. Smith, J. Org. Chem., 59, 6828 (1994).
M. Drogemuller, R. Jautelat, and E. Winterfeldt, Angew. Chem., Int. Ed. Engl., 35, 1572 (1996).
M. S. Mauhas, V. V. Rao, and S. G. Amin, J. Heterocycl. Chem., 13, 821 (1976).
B. P. Pradhan and P. Ghost, Indian J. Chem., Sect. B, 32, No. 5, 590 (1993).
P. Catsoulacos, J. Heterocycl. Chem., 10, 933 (1973).
B. Pfrunder and C. Tamm, Helv. Chim. Acta, 52, 6, 1630 (1969).
M. K. Ellis, B. T. Golding, A. B. Maude, and W. P. Watson, J. Chem. Soc., Perkin Trans. 1, 747 (1991).
D. H. R. Barton, R. A. H. F. Hui, D. J. Lester, and S. V. Ley, Tetrahedron Lett., 35, 3331 (1979).
K. Hattori, T. Yoshida, K. Rikuta, and T. Miyakoshi, Chem. Lett., 1885 (1994).
M. G. Moloney, D. R. Paul, R. M. Thompson, and E. Wright, Tetrahedron: Assymetry, 7,9, 2551 (1996).
R. V. Stevens, F. C. A. Gaeta, and D. S. Lawrence, J. Am. Chem. Soc., 105, 7713 (1983).
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 50–52, January–February, 2007.
Rights and permissions
About this article
Cite this article
Adamenko, E.N., Frolova, L.L., Panteleeva, M.V. et al. Synthesis of 1,11,11-trimethyl-3,6-diazotricyclo [6.2.1.02,7]undeca-2,6-diene and 1,15,15-trimethyl-3,10-diazotetracyclo[10.2.1.02,11.04,9]pentadeca-2,4(9),5,7,10-pentaene from camphoroquinone enantiomers. Chem Nat Compd 43, 59–62 (2007). https://doi.org/10.1007/s10600-007-0032-2
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10600-007-0032-2