An investigation of quinolizidine alkaloids by the optical rotatory dispersion (ORD) method
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1. The ORD curves of alkaloids of the sparteine, lupinine, and cytisine groups and of some derivatives of aphyllinic acid have been investigated. In the compounds investigated with an α-pyridone ring the epimers with the trans-quinolizidine linkage of the nuclei have a greater molecular amplitude than the corresponding cis isomers.
2. It has been shown that the alkaloids with a lactam group in an outer ring have higher molecular amplitudes than the corresponding compounds with the >N—C=O group in an inner ring. A dependence of the shape, sign, and molecular amplitude of the curves on the type of linkage of the quinolizidine nuclei and also a dependence of the molecular rotation of the position of a double bond in ring A or D have been given.
3. Derivatives of lupinine and of aphyllinic acid are characterized by curves approximating to a smooth shape with low-intensity anomalies, and in the case of the derivatives of aphyllinic acid studied they are shifted in the long-wave direction.
KeywordsCytisine Molecular Rotation Sparteine Quinolizidine Lupinine
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- 1.S. Iskandarov and S. Yunusov. Khim. Prirodn. Soedin., 494 (1970).Google Scholar
- 2.J. Skolik and M. Wiewiorowsky, Bull. Acad. Polon. Sci., Ser. Sci. Chim.,17, 201 (1969).Google Scholar
- 3.C. Djerassi, Optical Rotatory Dispersion, McGraw-Hill, New York (1960).Google Scholar
- 7.G. Snatzke, Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry, Heyden and Sons, London (1967).Google Scholar
- 12.P. M. Jones and W. Klyne, J. Chem. Soc.,1960, 871.Google Scholar
- 14.W. Crow, Austr. J. Chem.,12, 474 (1959).Google Scholar
- 17.K. Orazgil'diev, Kh. A. Aslanov, and A. S. Sadykov, Izvestiya AN Turkm SSR, Ser. Fiz. Tekh. i Khim. Nauk,6, 116 (1967).Google Scholar
- 18.Fam Khoang Nhok, Yu. K. Kushmuradov, Kh. A. Aslanov, and A. S. Sadykov, Trudy TashGU,3, No. 341, 99 (1968).Google Scholar