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Chemistry of Natural Compounds

, Volume 10, Issue 1, pp 49–54 | Cite as

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

  • M. R. Yagudaev
  • S. Yu. Yunusov
Article

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 E C-O 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.

Keywords

Alkaloid Furan Aromatic Proton Pyridine Ring Ring Current 

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Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • M. R. Yagudaev
  • S. Yu. Yunusov

There are no affiliations available

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