Skip to main content
Log in

Electronic structure and NMR spectra of some derivatives of furanquinoline, 5,6,7,8-tetrahydrofuranoquinoline, and dihydroquinolin-2-one alkaloids

Chemistry of Natural Compounds Aims and scope

Conclusions

1. The π charges, the bond orders, and the energy characteristics of 12 derivatives of furanoquinoline and dihydroquinolin-2-one alkaloids have been calculated by the MO LCAO method in Hückel's approximation.

2. It has been established that the CSs of the α- and β-protons of the furan ring are qualitatively comparable with the EDs on the corresponding carbon atoms C2 and C3, and the CSs of the aromatic protons of γ-fagarine and robustine do not correlate with the values of the EDs of the corresponding carbon atoms.

3. By performing quantitative calculations of the contributions due to the CSs, it has been shown that a substantial contribution is made to the CSs of H5 in γ-fagarine, robustine, and other related compounds by Δσr.c. of the pyridine ring and Δσ C-OE of the C-O bond of the OCH3 group at C4; the assignment of the signals of the aromatic protons of foliosidine has been refined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. A. V. Robertson, Austr. J. Chem.,16, 451 (1963).

    Article  CAS  Google Scholar 

  2. R. H. Prager, E. Ritchie, A. V. Robertson, and W. C. Taylor, Austr. J. Chem.,15, 301 (1962).

    Article  CAS  Google Scholar 

  3. S. R. Johns, J. A. Lamberton, and A. A. Simons, Austr. J. Chem.,20, 1975 (1967).

    Article  CAS  Google Scholar 

  4. M. R. Yagudaev and S. Yu. Yunusov, Khim. Prirodn. Soedin., 201 (1968).

  5. Z. Sh. Faizutdinova, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 360 (1968).

  6. I. A. Bessonova, Z. Sh. Faizutdinova, Ya. V. Rashkes, M. R. Yagudaev, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 273 (1969).

  7. D. Kurbanov, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 58, 373 (1968).

    Google Scholar 

  8. V. A. Tel'nov, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 724 (1970).

  9. D. M. Razzakova, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 133 (1972).

  10. S. M. Sharafutdinova and S. Yu. Yunusov, Khim. Prirodn. Soedin., 394 (1969).

  11. Z. Sh. Faizutdinova, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 455 (1969).

  12. B. Pullman and A. Pullman, Quantum Biochemistry, Wiley (1963).

  13. G. Fraenkel, R. E. Garter, N. McLachlan, and J. H. Richards, J. Amer. Chem. Soc.,82, 5846 (1960).

    Article  CAS  Google Scholar 

  14. H. Spiesecke and W. G. Shneider, Tetrahedron Lett., 468 (1961).

  15. G. G. Dvoryantseva, V. P. Lezina, V. F. Bystrov, T. N. Ul'yanova, G. P. Syrova, and Yu. N. Sheinker, Izv. Akad. Nauk SSR, Ser. Khim., No. 5, 994 (1968).

  16. A. H. Gawer and B. P. Dailey, J. Chem. Phys.,42, 2658 (1965).

    Article  CAS  Google Scholar 

  17. P. J. Black, R. A. Brown, and M. L. Heffernan, Austr. J. Chem.,20, 1305, 1325 (1967).

    Article  CAS  Google Scholar 

  18. T. B. Cobb and J. D. Memory, J. Chem. Phys.,50, 4262 (1969).

    Article  CAS  Google Scholar 

  19. G. G. Dvoryantseva, L. M. Alekseeva, T. N. Ul'yanova, Yu. N. Sheinker, P. M. Kochergin, and A. N. Krasovskii, Khim. Geterotsikl. Soedin., No. 7, 937 (1971).

  20. H. M. McConnell, J. Chem. Phys.,27, 226 (1957).

    Article  CAS  Google Scholar 

  21. A. D. Buckingham, Can. J. Chem.,38, 300 (1960).

    Article  CAS  Google Scholar 

  22. R. F. Zürcher, Progr. Nuc. Mag. Res. Spectrosc.2, Ch. 5 (1967).

  23. Yu. Yu. Samitov, Dokl. Akad. Nauk SSSR,164, 347 (1965).

    CAS  Google Scholar 

  24. A. V. Bogatskii, Yu. Yu. Samitov, N. L. Garkovik, and S. A. Andronati, Khim. Geterotsikl. Soedin., No. 2, 195 (1967).

Download references

Authors

Additional information

Order of the Red Banner of Labor Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 55–62, January–February, 1974.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yagudaev, M.R., Yunusov, S.Y. Electronic structure and NMR spectra of some derivatives of furanquinoline, 5,6,7,8-tetrahydrofuranoquinoline, and dihydroquinolin-2-one alkaloids. Chem Nat Compd 10, 49–54 (1974). https://doi.org/10.1007/BF00568221

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00568221

Keywords

Navigation