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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