SYNTHESIS OF NEW γ-LACTONE RING DERIVATIVES CONTAINING PYRIDINE AND TRICONDENSED SYSTEMS

Abstract

Lactone-pyridone rings contain many biologically active molecules of natural and artificial origin. The molecules contained in these two rings, represented by Cerpegine and its derivatives, will also exhibit high biological activity. It is also necessary to take into account that both natural and synthetic multi-substituted lactones have high biological activity. Thus, research in the field of multi-substituted lactones and further transformations are of particular interest. The synthesis of such systems began with the synthesis of a 2-acetylfuranone ring. In the next step, condensation of ethylcyanoacetate with 2-acetylfuranone by Knewenegel produced 3-substituted lactones, which according to the NMP 1H spectroscopy are a mixture of E and Z isomers. Then, when 3-substituted lactones were heated with dimethylformamide dimethylacetal DMFA/DMA, 3-substituted lactones containing a diene fragment in the structure were obtained. Stereoselective attachment E was detected using the NMR 1H spectrum. Then, under the action of the corresponding amine, the intermolecular substitution reactions produce compounds containing a lactone and pyridine group isolated by a σ-bond (serpegenous compound). Due to the proximity of the cyanide group of the pyridine ring and the fourth blight group of the lactone ring, intramolecular cyclization occurs during heating in the alkaline medium to form new tricondensed systems. Thus, an optimal method of synthesis of serpegenous compounds has been developed. These systems are of interest because in their skeleton they have not only a condensed system but also spirocycles. The connections themselves may be a promise for further exploration. For citation: Hakobyan R.M., Kharatyan L.A., Hayotsyan S.S., Attaryan H.S., Melikyan G.S. Synthesis of new γ-lactone ring derivatives containing pyridine and tricondensed systems. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2024. V. 67. N 7. P. 28-40. DOI: 10.6060/ivkkt.20246707.7068.