View PDF Version
 
DOI: 10.1039/A807233G (Paper) Reference Section for: Chem. Commun., 1998, 2387-2388

Cyclopenta[c]pyrans from 6-oxo-6H-1,3,4-oxadiazines†

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

Manfred Christl, Notker Bien, Gabriele Bodenschatz, Erich Feineis, Joachim Hegmann, Carola Hofmann, Stefan Mertelmeyer, Joachim Ostheimer, Frank Sammtleben, Susanne Wehner, Eva-Maria Peters, Karl Peters, Matthias Pfeiffer and Dietmar Stalke

Abstract

Prepared in a three-step sequence including acid-catalysed cycloaddition of cyclopentadiene to 6-oxo-6H-1,3,4-oxadiazines, dehydrogenation with DDQ of the dihydro-α-pyrones formed and reduction of the resulting α-pyrones with DIBAL-H, 1,4-disubstituted cyclopenta[c]pyrans are shown to undergo electrophilic substitution; the molecular structures of 1-(4-anisyl)-4-phenylcyclopenta[c]pyran and 4-isopropyl-1-phenylcyclopenta[c]pyran-7-carbaldehyde have been determined by single crystal X-ray diffraction studies.

References

  1. T. T. Tidwell, F. Sammtleben and M. Christl, J. Chem. Soc., Perkin Trans. 1, 1998, 2031 RSC.
  2. L. J. El-Naggar and J. L. Beal, J. Nat. Prod., 1980, 43, 649 CrossRef CAS; C. A. Boros and F. R. Stermitz, J. Nat. Prod., 1990, 53, 1055 CAS.
  3. (a) J. Meinwald, T. H. Jones, T. Eisner and K. Hicks, Proc. Natl. Acad. Sci. U. S. A., 1977, 74, 2189 CAS; (b) J. Meinwald and T. H. Jones, J. Am. Chem. Soc., 1978, 100, 1883 CrossRef CAS.
  4. (a) R.-P. Godeau, J.-C. Rossi and I. Fouraste, Phytochemistry, 1977, 16, 604 CrossRef CAS; (b) J.-L. Brayer, J.-P. Alazard and C. Thal, J. Chem. Soc., Chem. Commun., 1983, 257 RSC.
  5. T. Kämpchen, G. Moddelmog, D. Schulz and G. Seitz, Liebigs Ann. Chem., 1988, 855 Search PubMed.
  6. H. Kato, T. Kobayashi, M. Ciobanu, H. Iga, A. Akutsu and A. Kakehi, Chem. Commun., 1996, 1011 RSC; H. Kato, T. Kobayashi, M. Ciobanu and A. Kakehi, Tetrahedron, 1997, 53, 9921 CrossRef CAS.
  7. Review on pseudoazulenes: H.-J. Timpe and A. V. El'tsov, Adv. Heterocycl. Chem., 1983, 33, 185 Search PubMed.
  8. M. Christl, G. Bodenschatz, E. Feineis, J. Hegmann, G. Hüttner, S. Mertelmeyer, K. Schätzlein and H. Schwarz, J. Prakt. Chem., 1995, 337, 659 CrossRef CAS.
  9. Preparation of the oxadiazinone 6a: W. Steglich, E. Buschmann, G. Gansen and L. Wilschowitz, Synthesis, 1977, 252 Search PubMed the other oxadiazinones 6, except 6e(preparation as that of 6d), have been described in the previous papers of this series.
  10. J. Hegmann, E. Ditterich, G. Hüttner, M. Christl, E.-M. Peters, K. Peters and H. G. von Schnering, Chem. Ber., 1992, 125, 1913 CAS.
  11. O. Bastiansen and J. L. Derissen, Acta Chem. Scand., 1966, 20, 1319 CAS and references cited therein.
Click here to see how this site uses Cookies. View our privacy policy here.