Investigation objects: aromatic amines, amioazoles, aminoazines, aldehydes, 1.3-dicarbonyl compounds, 9,10-R,R'-acridinediones, pyrido[2,3-d]pyrimidine-2,4-, pyrimido[4,5-b]quinoline-4,6-diones, pyrazolo[3,4-b]quinoline-5-, pyrazolo[5,1-b]quinazoline-8-, pirazolo[4,3-c] quinolizin-9-ones, pyrazolo[5,1-b] uinazoline-3-, pyrazolo[1,5-a]quinolin-3-, imidazo[1,2-a]pyrimidines. Objectives: study of linear and multicomponent heterocyclization reactions involving carbonyl containing active methylene compounds, aldehydes and some binuclephiles, detection of their regularities and searching for ways to control positional, regio- and chemodirection, development of novel methods for selective synthesis of fused pyridine and pyrimidine derivatives. Methods and apparatus: organic synthesis, NMR spectroscopy, mass- spectrometry, X-ray analysis, high-performance liquid chromatography (HPLC), elemental analysis. Theoretical and practical results: It was found the general regularities of the heterocyclizations studied and influence of parameters of the reactions on their direction. Selective pathways to the synthesis of fused pyridine and pyrimidine derivatives were elaborated as well. It was established that heterocyclizations studied can pass in four main directions with formation of different classes of heterocyclic systems. The regularities established for the reactions of carbonyl containing CH-acids, aldehydes and binucleophiles allowed, by changing temperature, type of catalytic system and structure of starting materials, controlling direction of heterocycloizations. Novelty: It was discovered new multicomponent reaction passing via unusual rearrangement with opening cycloalkanone moiety and leading to formation of pyrazoloqunalizinones being analogues of natural alkaloids. It was shown that the increase in yields and purity of the products of cyclocondensation of aminoazole, cyclic 1,3-diketones and aldehydes under microwave irradiation is associated with the optimization of the temperature profile of the interaction. Application field: Laboratories and the Departments of various educational and scientific organizations, carrying out study of similar objects and research centers dealing with biological active compounds.
