The dissertation is devoted to the experimental and DFT studies of the reactivity of azo-bis-4,6-dichloro-1,3,5-triazine in the Diels-Alder reaction and the synthesis of new nitrogen-containing heterocycles on its basis, studying their chemical properties for further modification and studying biological activity of the obtained compounds. The Diels-Alder reaction of azo-bis-cyanuric chloride and a series of 1,3-dienes to give the corresponding 6,6`-(3,4,5-substituted-3,6-dihydropyridazine-1,2-diyl)bis(2,4-dichloro-1,3,5-triazines), and with anthracene to form 11,12-triazine-9,10-epidiazanoanthracene was investigated. The conditions of nucleophilic substitution of the obtained products chlorine atoms have been established. It was shown that the interaction of azo-bis-cyanuric chloride with cyclohexane-1,3-diene does not produce the Diels-Alder reaction product, instead of the addition of azo-bis-cyanuric chloride and the disclosure of the cyclohexadenic cycle to form the product with hexa-2,5-diene chain – (E)-6,6'-(1-(hexa-2,5-dien-1-yl)hydrazine-1,2-diyl)bis(2,4-dichloro-1,3,5-triazine). The reactivity of azo-bis-cyanuric chloride as an electron-deficient diene in an IED Diels-Alder reaction was shown. By the modeling on M06-2X/6-31G(d,p) level, it was found that the reaction with furan and styrene proceeds in two stages, with the initial formation of the NED Diels-Alder reaction product and its subsequent [3,3] sigmatropic rearrangement in thermodynamically stable formal IED Diels-Alder reaction product. In the interaction of azo-bis-cyanuric chloride with vinyl compounds, the formation of the IED Diels-Alder reaction product takes place in one step. The screening of antimicrobial activity showed that a number of synthesized compounds have a pronounced activity in relation to Staphylococcus aureus, Mycobacterium luteum, Aspergillus niger and Candida tenuis. Any of the synthesized compounds is not characterized by the activity in relation to Escherichia coli.
