Chemistry of Heterocyclic Compounds

, Volume 48, Issue 7, pp 997–1005 | Cite as

Synthesis and reactivity of methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2-carboxylates

  • V. P. Sheverdov
  • A. Yu. Andreev
  • O. V. Ershov
  • O. E. Nasakin
  • V. A. Tafeenko
  • V. L. Gein
Article
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By treating arylidenemalononitriles with methyl 2,4-dioxobutanoates, derivatives of 4H-pyrans - methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2-carboxylates - are obtained, which are novel, promising structural components for the synthesis of carbo- and heterocycles. The reactions of these pyrans with sulfuric and hydrochloric acids, acetic anhydride, and alcohols have been studied. Novel methods have been developed for the preparation of substituted derivatives of cyclopentenone, pyrano[2,3-d]-pyrimidine, 5-oxo-3-phenylpentanoic acid, and nicotinic acid nitrile.

Keywords:

cyclopentenones 5-oxopentanoic acid 4H-pyrans pyridines ring opening 
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References

  1. 1.
    O. A. Fathalla, S. M. Awad, and M. S. Mohamed, Arch. Pharm. Res., 28, 1205 (2005).CrossRefGoogle Scholar
  2. 2.
    F. A. Eid, A. H. F. Abd El-Wahab, G. A. M. El-Hag Ali, and M. M. Khafagy, Acta Pharm., 54, 13 (2004).Google Scholar
  3. 3.
    A. G. Martinez and L. J. Marco, Bioorg. Med. Chem. Lett., 7, 3165 (1997).CrossRefGoogle Scholar
  4. 4.
    K. C. Joshi, R. Jain, and K. Sharma, J. Indian Chem. Soc., 65, 202 (1988); Chem. Abstr., 109, 149464 (1988).Google Scholar
  5. 5.
    A. E. Amr, A. M. Mohamed, S. F. Mohamed, N. A. Abdel-Hafez, and A. G. Hamman, Bioorg. Med. Chem., 14, 5481 (2006).CrossRefGoogle Scholar
  6. 6.
    I. V. Magedov, M. Manpadi, M. A. Ogasawara, A. S. Dhawan, S. Rogelj, S. Van Slambrouck, W. F. A. Steelant, N. M. Evdokimov, P. Y. Uglinskii, E. M. Elias, E. J. Knee, P. Tongwa, M. Yu. Antipin, and A. Kornienko, J. Med. Chem., 51, 2561 (2008).CrossRefGoogle Scholar
  7. 7.
    S. X. Cai, H. Zhang, S. Jiang, and R. Storer, US Pat. Appl. 7053117.Google Scholar
  8. 8.
    A. C. Williams, US Pat. Appl. 5571818.Google Scholar
  9. 9.
    A. H. Abdel-Rahman, E. M. Keshk, M. A. Hanna, and Sh. M. El-Bady, Bioorg. Med. Chem., 12, 2483 (2004).CrossRefGoogle Scholar
  10. 10.
    V. V. Mulwad and C. A. Patil, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 44B, 2355 (2005).Google Scholar
  11. 11.
    K. C. Joshi, R. Jain, and S. Arora, J. Indian Chem. Soc., 65, 277 (1988); Chem. Abstr., 109, 190180 (1988).Google Scholar
  12. 12.
    A. V. Milyutin, N. V. Safonova, R. R. Makhmudov, Yu. S. Andreichikov, and E. G. Aliev, Khim.-Farm. Zh., 32, No. 1, 27 (1998).Google Scholar
  13. 13.
    V. L. Gein, L. F. Gein, N. Yu. Porseva, E. V. Voronina, M. I. Vakhrin, K. D. Potemkina, V. E. Kolla, L. P. Drovosekova, A. V. Milyutin, N. S. Shchuklina, and G. A. Veikhman, Khim.-Farm. Zh., 32, No. 9, 23 (1998).Google Scholar
  14. 14.
    V. L. Gein, A. V. Demeneva, N. A. Rassudikhina, and M. I. Vakhrin, Zh. Org. Khim., 42, 634 (2006).Google Scholar
  15. 15.
    V. L. Gein, N. A. Rassudikhina, and E. V. Voronina, Khim.-Farm. Zh., 40, No. 10, 32 (2006).Google Scholar
  16. 16.
    V. P. Sheverdov, O. E. Nasakin, A. Yu. Andreev, V. L. Gein, and V. A. Tafeenko, Zh. Org. Khim., 47, 1097 (2011).Google Scholar
  17. 17.
    K. M. Brummond and D. Chen, Org. Lett., 10, 705 (2008).CrossRefGoogle Scholar
  18. 18.
    E. Leclerc and M. A. Tius, Org. Lett., 5, 1171 (2003).CrossRefGoogle Scholar
  19. 19.
    R. C. Cambie, P. S. Rutledge, R. J. Stevenson, and P. D. Woodgate, J. Organometallic Chem., 471, 133 (1994).CrossRefGoogle Scholar
  20. 20.
    L. F. Tietze, Th. Eicher, U. Diederichsen, and A. Speicher, Reactions and Syntheses in the Organic Chemistry Laboratory, Wiley-VCH, Weinheim (2007), p. 16.Google Scholar
  21. 21.
    A. Attia and M. Michael, Acta Chim. Hung., 112, 89 (1983); Chem. Abstr., 99, 88006 (1983).Google Scholar
  22. 22.
    M. N. Jachak, D. B. Kendre, A. B. Avhale, R. B. Toche, and R. W. Sabnis, J. Heterocycl. Chem., 44, 1525 (2007).CrossRefGoogle Scholar
  23. 23.
    K. Harms and S. Wocadlo, XCAD-4: Program for Processing CAD-4 Diffractometer Data, University of Marburg (1995).Google Scholar
  24. 24.
    G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).CrossRefGoogle Scholar
  25. 25.
    K. Brandenburg, DIAMOND, Release 2.1d, Crystal Impact GbR, Bonn (2000).Google Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • V. P. Sheverdov
    • 1
  • A. Yu. Andreev
    • 1
  • O. V. Ershov
    • 1
  • O. E. Nasakin
    • 1
  • V. A. Tafeenko
    • 2
  • V. L. Gein
    • 3
  1. 1.Chuvashia State University named after I. N. UlyanovCheboksaryRussia
  2. 2.M. V. Lomonosov Moscow State UniversityMoscowRussia
  3. 3.Perm’ State Pharmaceutical AcademyPerm’Russia

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