Synthesis of mixed heteroatom wurtzitanes

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Hiroshi Izumi and Shigeru Futamura


Abstract

Syntheses of a novel series of mixed heteroatom wurtzitanes (tetracyclo[5.3.1.12,6.04,9]dodecanes) are described. cis,cis-1,3,5-Triformyl-1,3,5-trimethylcyclohexane 3 reacts with equimolar amounts of primary amines to afford the structurally novel 1,7,9-trimethyl-3,5-dioxa-12-azawurtzitanes, containing two different heteroatoms in the wurtzite ring. The mechanism for the reaction of compound 3 with primary amines in CHCl3 is also reported.


References

  1. B. Greener, M. H. Moore and P. H. Walton, Chem. Commun., 1996, 27 RSC.
  2. S. de Angelis, A. Batsanov, T. J. Norman, D. Parker, K. Senanayake and J. Vepsalainen, J. Chem. Soc., Chem. Commun., 1995, 2361 RSC.
  3. C. Raposo, M. Almaraz, M. Martín, V. Weinrich, M. L. Mussóns, V. Alcázar, M. C. Caballero and J. R. Morán, Chem. Lett., 1995, 759 CAS.
  4. L. Casella, M. Gullotti, G. Pallanza and L. Rigoni, J. Am. Chem. Soc., 1988, 110, 4221 CrossRef CAS.
  5. H. Izumi, O. Setokuchi, Y. Shimizu, H. Tobita and H. Ogino, J. Org. Chem., 1997, 62, 1173 CrossRef CAS.
  6. R. O. Klaus, H. Tobler and C. Ganter, Helv. Chim. Acta, 1974, 57, 2517 CAS; D. P. G. Hamon, G. F. Taylor and R. N. Young, Aust. J. Chem., 1977, 30, 589 CAS; R. O. Klaus and C. Ganter, Helv. Chim. Acta, 1980, 63, 2559 CAS.
  7. A. T. Nielsen, S. L. Christian, D. W. Moore, R. D. Gilardi and C. F. George, J. Org. Chem., 1987, 52, 1656 CrossRef CAS.
  8. V. J. Baker, I. J. Ferguson, A. R. Katritzky, R. Patel and S. Rahimi-Rastgoo, J. Chem. Soc., Perkin Trans. 2, 1978, 377 RSC.
  9. H. Spiesecke and W. G. Schneider, J. Chem. Phys., 1961, 35, 722 CrossRef CAS; B. P. Dailey and J. N. Shoolery, J. Am. Chem. Soc., 1955, 77, 3977 CrossRef CAS; E. C. Friedrich and K. G. Runkle, J. Chem. Educ., 1984, 61, 830 CAS; 1986, 63, 127.
  10. K. Fujimori, H. Yoshimoto and S. Oae, Tetrahedron Lett., 1980, 21, 3385 CrossRef CAS.
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