Summary
1. The furanoquinoline alkaloids skimmianine, haploperine, and γ-fagarine are reduced at a dropping mercury electrode in 0.1 N (C2H5)4NI and (C2H5)4NOH in 80% ethanol forming tetrahydro or hexahydro derivatives according to the potential of the electrode.
2. Carbostyryl and N-methylcarbostyryl are reduced under the same conditions to the corresponding dihydro derivatives.
3. The proposed mechanism for the electrode processes is confirmed by a comparison of the UV and IR spectra of the substances before and after their electrolysis at a controlled potential with the spectra of synthetic compounds.
Similar content being viewed by others
References
E. K. Dobronravova and A. L. Markman, Uzb. khim. zh., no. 2, 31, 1965.
E. K. Dobronravova and A. L. Markman, KhPS [Chemistry of Natural Compounds], 333, 1966.
A. G. Stromberg and T. M. Makaricheva, ZhOKh,28, 671, 1954.
L. Lingane, J. Am. Chem. Soc.,67, 1917, 1945.
T. Ota, RZhKhim, 32454, 1954.
A. E. Chichibabin, ZhRKhO,55, 7, 1924.
J. Cavallito and T. H. Haskell, J. Am. Chem. Soc.,66, 1166, 1944.
I. M. Koltooff and J. J. Lingane, Polarography [Russian translation], 62, 1948.
R. G. Cooke and H. F. Haynes, Austr. J. Chem.,7, 273, 1954.
L. H. Briggs and L. D. Colebrook, J. Chem. Soc., 2458, 1960.
L. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], Moscow, 196, 1963.
G. P. Sidyakin et al., ZhOKh,32, 409, 1962.
I. A. Bessonova, G. P. Sidyakin, and S. Yu. Yunusov, DAN UzSSR, no. 10, 33, 1959; no. 1, 50, 1962.
T. T. Shakirov, G. P. Sidyakin, and S. Yu. Yunusov, DAN UzSSR, no. 9, 40, 1960; no. 8, 47, 1961.
V. I. Pastukhova, G. P. Sidyakin, and S. Yu. Yunusov, DAN UzSSR, no. 7, 31, 1964; KhPS [Chemistry of Natural Compounds], 27, 1965.
Author information
Authors and Affiliations
Additional information
Khimiya Prirodnykh Soedinenii, Vol. 3, No. 4, pp. 253–257, 1967
Rights and permissions
About this article
Cite this article
Dobronravova, E.K., Markman, A.L. Mechanism of the reduction of the alkaloids ofHaplophyllum at a dropping mercury electrode. Chem Nat Compd 3, 212–214 (1967). https://doi.org/10.1007/BF00564118
Issue Date:
DOI: https://doi.org/10.1007/BF00564118