Vinyltriphenylphosphonium Salt Mediated One-pot Synthesis of Dialkyl 5-formyl-2H-pyran-2,3-dicarboxylate

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Ahmad Shaabani and Faizeh Sadeghi Nejat


Abstract

Protonation of the highly reactive 1:1 intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by triformylmethane leads to vinyltriphenylphosphonium salts which undergo an intramolecular Wittig reaction to produce dialkyl 5-formyl-2H-pyran-2,3-dicarboxylates in fairly high yields.


References

  1. J. Kuthan, Adv. Heterocycl. Chem., 1983, 34, 145 CAS.
  2. J. Kuthan, P. Sebek and S. Boehm, Adv. Heterocycl. Chem., 1995, 62, 19 CAS.
  3. K. Bogdanowicz-Szwed and A. Palasz, Wiad. Chem., 1996, 50, 213 (Chem. Abstr., 1996, 125, 221451z) Search PubMed.
  4. K. B. Becker, Tetrahedron, 1980, 36, 1717 CrossRef CAS.
  5. I. Yavari and A. Ramazani, J. Chem. Res. (S), 1996, 332 Search PubMed.
  6. I. Yavari and R. Baharfar, Tetrahedron Lett., 1997, 38, 4259 CrossRef CAS.
  7. I. Yavari, A. Ramazani and A. Yahyz-Zadeh, Chem. Commun., 1996, 4495 Search PubMed.
  8. K. C. Nicolaou, M. W. Harter, J. L. Gunzner and A. Nadin, Liebigs Ann., 1997, 1283 Search PubMed.
  9. Z. Arnold and M. Budesinsky, J. Org. Chem., 1988, 53, 5352 CrossRef CAS.
  10. M. Keshavarz-K, S. D. Cox, R. O. Angus Jr. and F. Wudl, Synth. Commun., 1988, 641 CAS.
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