Reaction between Alkyl Isocyanides and Dimethyl Acetylenedicarboxylate in Presence of N,N′-Dimethylbarbituric Acid. A Convenient Route to Highly Functionalized 4H-Pyrano[3,2-d]pyrimidine Derivatives

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Issa Yavari and Malek Taher Maghsoodlou


Abstract

The highly reactive 1:1 intermediate produced in the reaction between alkyl isocyanides and dimethyl acetylenedicarboxylate is trapped by N,N′-dimethylbarbituric acid to yield 4H-pyrano[3,2-d]pyrimidine derivatives in fairly high yields.


References

  1. I. Ugi, Isonitrile Chemistry, Academic Press, London, 1971 Search PubMed.
  2. I. Ugi, Angew. Chem., Int. Ed. Engl., 1982, 21, 810 CrossRef.
  3. H. M. Walborsky and M. P. Persiasamy, in The Chemistry of Functional Groups, Supplement C, ed. S. Patai and Z. Rappopors, Wiley, New York, 1983, ch. 20, pp. 835–887 Search PubMed.
  4. S. Marcaccini and T. Torroba, Org. Prep. Proced. Int., 1993, 25, 141 CAS.
  5. T. R. Oakes and D. J. Donovan, J. Org. Chem., 1973, 38, 1319 CrossRef CAS.
  6. R. Huisgen, K. Herbig, A. Siegl and H. Huber, Chem. Ber., 1966, 99, 2526 CAS.
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