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DOI: 10.1039/A605368H (Paper) Reference Section for: J. Chem. Res. (S), 1997, 84-85

1-Substituted 3-Dimethylaminoprop-2-en-1-ones as Building Blocks in Heterocyclic Synthesis: Routes to 6-Aryl- and 6-Heteroaryl-2H-pyran-2-ones and 6- and 4-Arylpyridin-2(1H)-ones

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Fatima Al-Omran, Nouria Al-Awadhi, Mervat Mohammed Abdel Khalik, Kamini Kaul, Abdel Abu EL-Khair and Mohammed Hilmy Elnagdi

Abstract

Several new 6-substituted-3-acylamino-2H-pyran-2-ones 6a–j have been prepared from the reaction of enaminones 4a–f with N-acyl- and N-benzoyl-glycines; the enaminones 4a–c react with malononitrile in ethanol solution and in the presence of a base to yield amides 11a–c which are converted into 6-aryl-1,2-dihydro-2-oxypyridine-3-carbonitriles 13a–c on reflux in acetic acid.

References

  1. H. Al-Awadhi, F. Al-Omran, M. H. Elnagdi, L. Infants, C. Foces-Foces, N. Jagerovic and J. Elguero, Tetrahedron, 1995, 51, 12 745 CrossRef CAS.
  2. M. H. Elnagdi, A. H. Elghandour, M. K. A. Ibrahim and I. S. A. Hafiz, Z. Naturforsch., 1992, 476, 572 Search PubMed.
  3. F. A. Abou-Shanab, M. H. Elnagdi, F. M. Ali and B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1, 1994, 1449 RSC.
  4. M. H. Elnagdi and A. W. Erian, Arch. Pharm. (Weinheim, Ger.), 1991, 324, 853 Search PubMed.
  5. J. D. Hepworth, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, vol. 3, pp. 737–883 Search PubMed.
  6. V. Kepe, M. Kocevar and S. Polance, Heterocycles, 1995, 41, 1299 CAS.
  7. M. Kocevar, S. Polance, B. Vercek and M. Tisler, Liebigs Ann. Chem., 1990, 501 Search PubMed.
  8. V. Kepe, M. Kocevar, S. Polance, B. Vercek and M. Tisler, Tetrahedron, 1990, 46, 1081 CrossRef CAS.
  9. S. Tseng, J. W. Epstein, H. J. Brbander and G. Francisco, J. Heterocycl. Chem., 1987, 24, 837 CAS.
  10. A. A. Elagamey, F. M. A. El Taweel, S. Z. A. Sowellium, M. A. Sofan and M. H. Elnagdi, Collect. Czech. Chem. Commun., 1990, 55, ??? CAS.
  11. M. H. Elnagdi, R. M. Abdel-Motaleb, M. Mustafa, M. F. Zayed and E. M. Kamel, J. Heterocycl. Chem., 1987, 24, 1677 CAS.
  12. C. P. Dell, T. J. Howe and W. C. Prowe, J. Heterocycl. Chem., 1994, 31, 749 CAS.
  13. B. J. N. Martin, A. Martinez-Grau and C. Seoane, J. Heterocycl. Chem., 1995, 32, 1381.
  14. N. M. Abed, N. S. Ibrahim and M. H. Elnagdi, Z. Naturforsch., 1986, 416, 925 Search PubMed.
  15. F. Al-Omran, M. M. Abdel Khalik and M. H. Elnagdi, Heteroatom Chem., 1995, 6, 545 CrossRef CAS.