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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 8, pp 946–952 | Cite as

Reaction of methyl 3-[(dimethylamino)methylidene]-6-fluoro-4-oxo −3,4-dihydrochroman-2-carboxylate with primary and secondary amines*

  • A. I. Kysil
  • V. S. Moskvina
  • A. V. Turov
  • Z. V. Voitenko
  • V. P. Khilya
Article

A method was developed for substitution of the dimethylamino group by bioisosteric fragments by the action of various primary and secondary amines on methyl 3-[(dimethylamino)methylidene]-6-fluoro-4-oxo-3,4-dihydrochroman-2-carboxylate.

Keywords

3-aminomethylidenechroman-4-one primary and secondary amines chroman bioisosteric displacements. 

References

  1. 1.
    Ø. M. Andersen and К. R. Markham, Flavonoids: Chemistry, Biochemistry, and Applications, CRC, Taylor & Francis, Boca Raton, FL, 2006.Google Scholar
  2. 2.
    A. R. Katritzky (editor), Comprehensive Heterocyclic Chemistry III, Vol. 6. Six-membered Rings with One Heteroatom, Ch. 7–9, Elsevier, 2008.Google Scholar
  3. 3.
    L. Mosti, P. Schenone, and G. Menozzi, J. Heterocycl. Chem., 17, 61 (1980).CrossRefGoogle Scholar
  4. 4.
    P. F. Schuda, C. B. Ebner, and T. M. Morgan, Tetrahedron Lett, 27, 2567 (1986).CrossRefGoogle Scholar
  5. 5.
    A. H. Bedair, Y. A. Ammar, A. M. El-Agrody, and Y. A. Mohamed, Proc. Indian Natl. Sci. Acad., Part B, 53, 308 (1987).Google Scholar
  6. 6.
    M.-C. Bellassoued-Fargeau, B. Graffe, M.-C. Sacquet, and P. Maitte, J. Heterocycl. Chem., 22, 713 (1985).CrossRefGoogle Scholar
  7. 7.
    H. An, S.-J. Eum, M. Koh, S. K. Lee, and S. B. Park, J. Org. Chem., 73, 1752 (2008).CrossRefGoogle Scholar
  8. 8.
    Ch. Wu, H. Zeng, L. Liu, D. Wang, and Y. Chen, Tetrahedron, 67, 1231 (2011).CrossRefGoogle Scholar
  9. 9.
    F. D. King (editor), Medicinal Chemistry: Principles and Practice, Royal Society of Chemistry, Cambridge, 2002.Google Scholar
  10. 10.
    E. Ziegler, G Henning, and A. K. Muller, Liebigs Ann. Chem., 1552 (1973).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • A. I. Kysil
    • 1
  • V. S. Moskvina
    • 1
  • A. V. Turov
    • 1
  • Z. V. Voitenko
    • 1
  • V. P. Khilya
    • 1
  1. 1.Taras Shevchenko Kyiv National UniversityKyivUkraine

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