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Synthesis and Stereochemistry of New N-Substituted Cytisine Derivatives

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Abstract

A series of new N-substituted cytisine derivatives was synthesized. The 1 H and 13 C NMR spectra of certain compounds exhibit a doubled set of signals. This is explained by formation of diastereomeric pairs in compounds containing an asymmetric center in the substituents. The signal splitting in -COHC=CHCO 2 H and HC=O (formyl) derivatives is explained by the existence of Z and E invertomers. Their stereochemical features are discussed. Amide conjugation is confirmed by temperature experiments.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, 450054, Ufa, Prospekt Oktyabrya 71

    T. V. Khakimova, O. A. Pukhlyakova, G. A. Shavaleeva, A. A. Fatykhov, E. V. Vasil'eva & L. V. Spirikhin

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  1. T. V. Khakimova
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  2. O. A. Pukhlyakova
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  3. G. A. Shavaleeva
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  4. A. A. Fatykhov
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  5. E. V. Vasil'eva
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  6. L. V. Spirikhin
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Khakimova, T.V., Pukhlyakova, O.A., Shavaleeva, G.A. et al. Synthesis and Stereochemistry of New N-Substituted Cytisine Derivatives. Chemistry of Natural Compounds 37, 356–360 (2001). https://doi.org/10.1023/A:1013778703658

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