SYNTHESIS AND STRUCTURED N-ACYL AND THIOUREA DERIVATIVES CITIZINE AND ANABAZINE

Abstract

This work presents the results of studies on the chemical transformation of the alkaloids moleculescytisine and anabazine to obtain their N-cinnamoyl derivatives, as well as possible ways for their furthermodification. The optimal conditions for the preparation of N-cinnamoylcytisine and N-cinnamoylanabazine in theacylation reactions of alkaloids with cinnamoyl chloride are considered. Hydrazinolysis of the resulting Ncinnamoylcytisine and N-cinnamoylanabazine was carried out. It was shown that the interaction of acrylamidederivatives of alkaloids with hydrazine hydrate in ethanol leads to the formation of the corresponding pyrazolederivatives resulting from the intramolecular cyclocondensation of hydrazones of N-cinnamoyl derivatives. By theinteraction of cinnamoylisothiocyanate with the above alkaloids, new thiourea derivatives are synthesized. Thestructures of the synthesized compounds were studied by 1H and 13C NMR spectroscopy, as well as by the data oftwo-dimensional spectra of COSY (1H-1H) and HMQC (1H-13C). The values of chemical shifts, multiplicity, andintegrated intensity of 1H and 13C signals in one-dimensional NMR spectra were determined. Using spectra in theformats COSY (1Н1Н) and HMQC (1Н13С), homo- and heteronuclear interactions were established, confirming thestructure of the studied compounds