An investigation of quinolizidine alkaloids by the optical rotatory dispersion (ORD) method
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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