SYNTHESIS OF SUBSTITUTED TETRAHYDROBENZO [B] [1,6]NAPHTHYRIDINES AND RESEARCHING OF THEIR INTERACTION WITH ACTIVATED ALKINES

Benzonaphthyridines are a very important class of heterocyclic compounds. The duality of the chemical structure, namely the presence of a quinoline and pyridine fragment, makes it possible to use these molecules as active substances in the field of pharmacological control of Alzheimer's and Parkinson's disease. However, in modern scientific knowledge about benzonaftiridines, theoretical foundations are favored over practical ones. Only 3 methods of synthesis of benzonaphthyridines have been studied: according to Pfinger, Frinndler and the heterocycle-heterocyclic method. Syntheses according to these methods have a significant drawback, which contains a radical oversaturation of the resulting structures, which does not allow further chemical modifications to be freely performed. The functionalization of substituted benzonaphthyridines is a key process for the accumulation of experimental knowledge in the study of chemical and biological properties of these compounds. However, the available results describe the interactions of these substances with a very limited range of molecules introduced into the structure of benzonaphthyridines as radical functional groups. In connection with this, the purpose of this article was the synthesis of substituted tetrahydrobenzonaphthyridines and the study of their interaction with activated alkynes. The objectives of this study were: conducting a sequential synthesis consisting of 4 stages, describing the alleged mechanisms of previously unknown reactions. This article is an original research, the objects of which were substituted benzonaphthyridines. All components of the reactions produced in this study were selected according to criteria determined according to the available conditions for conducting experimental reactions. All reactions were carried out using classical methods of organic chemistry, all the compounds obtained were investigated using physico-chemical methods. In the course of this work, a method was proposed for the functionalization of N-substituted tetrahydrobenzo[b][1,6]naphthyridines with 3,4-R-phenylacetylenes (R=H, OME, F, CF3). The interaction of unsubstituted and functionalized benzonaphthyridines with acetylenes has been studied. During the conducted reactions, it was determined that unsubstituted tetrahydrobenzo[b][1,6]naphthyridines were inert in reactions of this type, and 2 target addition products according to Michael and Hoffman were obtained from phenylethyl derivatives