Advertisement

Chemistry of Heterocyclic Compounds

, Volume 28, Issue 11, pp 1236–1244 | Cite as

Synthesis of heterocycles based on the products of the addition of polyhalogenoalkanes to unsaturated systems. 3. Structure and stereochemistry of substituted N-furylformamidines

  • D. M. Antonov
  • L. I. Belen'kii
  • V. S. Bogdanov
  • A. A. Dudinov
  • M. M. Krayushin
  • V. N. Nesterov
  • Yu. T. Struchkov
  • B. I. Ugrak
Article
  • 31 Downloads

Abstract

It was established with the aid of the 1H, 13C, and 15N NMR spectra as well as the x-ray structural analysis that the substituted furylformamidines, which are key compounds in the synthesis of furo[2,3-d]pyrimidines, are E-isomers of N(1) -furyl-N(2) -R-formamidines (R=H, Alk, Ar), independently of the nature of the substituent at the second N atom, and occur mainly in the form of the antiplanar rotamers.

Keywords

Organic Chemistry Structural Analysis Pyrimidine Unsaturated System 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. A. Dudinov, L. I. Belen'kii, V. S. Bogdanov, B. I. Ugrak, and M. M. Krayushkin, Khim. Geterotsikl. Soedin., No. 9, 1250 (1990).Google Scholar
  2. 2.
    D. M. Antonov, L. I. Belen'kii, V. S. Bogdanov, A. A. Dudinov, B. I. Ugrak, and M. M. Krayushkin, The Chemistry and Technology of Furan Compounds. Synthesis, Stereochemistry, and Properties of Furan Derivatives: Inter-College Symposium of Scientific Work, Krasnodar (1990), p. 21.Google Scholar
  3. 3.
    M. Ono, R. Todoriki, and S. Tamura, Chem. Pharm. Bull., 38, 866 (1990).Google Scholar
  4. 4.
    J. Oszczapowicz, E. Raczynska, and J. Osek, Magn. Res. Chem., 24, 9 (1986).Google Scholar
  5. 5.
    A. F. Hegarty and O. Chandler, Tetrahedron Lett., 21, 885 (1990).Google Scholar
  6. 6.
    G. C. Levy and R. L. Lichter, Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy, J. Wiley, New York (1979), p. 221.Google Scholar
  7. 7.
    G. Binch, J. B. Lambert, B. W. Roberts, and J. D. Roberts, J. Am. Chem. Soc., 86, 5564 (1964).Google Scholar
  8. 8.
    H. J. C. Yen, H. Ziffer, D. M. Jerina, and D. R. Boyd, J. Am. Chem. Soc., 95, 2741 (1973).Google Scholar
  9. 9.
    D. Crepaux and J.-M. Lehn, Org. Magn. Res., 7, 524 (1975).Google Scholar
  10. 10.
    J. P. Kintzinger and J.-M. Lehn, Chem. Commun., No. 13, 660 (1967).Google Scholar
  11. 11.
    A. K. Bose and J. Kugajevsky, Tetrahedron, 23, 1480 (1967).Google Scholar
  12. 12.
    G. J. Martin, M. L. Martin, and J.-P. Gouesnard, 15N-NMR Spectroscopy, Springer-Verlag, Berlin (1981), p. 191.Google Scholar
  13. 13.
    R. R. Fraser and M. Bresse, Can. J. Chem., 61, 576 (1983).Google Scholar
  14. 14.
    V. M. S. Gil and W. V. Philipsborn, Magn. Res. Chem., 27, 409 (1989).Google Scholar
  15. 15.
    M. Drobnic-Koserok, S. Polanc, B. Stanovnik, M. Tisler, and B. Vercek, J. Heterocycl. Chem., 15, 1105 (1978).Google Scholar
  16. 16.
    I. Wawer, Magn. Res. Chem., 26, 601 (1988).Google Scholar
  17. 17.
    H. Shonan-Atidi and K. H. Bar-Ell, J. Phys. Chem., 74, 961 (1970).Google Scholar
  18. 18.
    F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin II, No. 12, 51 (1987).Google Scholar
  19. 19.
    O. Exner, M. Bodesinsky, D. Hnyk, V. Vsetecka, and E. D. Raczynska, J. Mol. Struct., 178, 147 (1988).Google Scholar
  20. 20.
    J. W. Krajewski, Z. Urbanczyk-Lipkowska, P. Gluzinski, J. Busko-Ostapowicz, J. Bleidelis, and A. Kemme, Pol. J. Chem., 55, 1015 (1981).Google Scholar
  21. 21.
    D. Hall, Acta Cryst., 18, 955 (1965).Google Scholar
  22. 22.
    A. Bondi, J. Phys. Chem., 70, 3006 (1966).Google Scholar
  23. 23.
    G. A. Morris and R. Freeman, J. Magn. Res., 101, 760 (1979).Google Scholar
  24. 24.
    K. G. Pachler and P. G. Wessels, J. Magn. Res., No. 12, 377 (1973).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • D. M. Antonov
    • 1
  • L. I. Belen'kii
    • 1
  • V. S. Bogdanov
    • 1
  • A. A. Dudinov
    • 1
  • M. M. Krayushin
    • 1
  • V. N. Nesterov
    • 1
  • Yu. T. Struchkov
    • 1
  • B. I. Ugrak
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryRussian Academy of SciencesMoscow

Personalised recommendations