Abstract: At present, polyazacyclic compounds (nitrogen-containing heterocyclic structures) are considered as synthons in the synthesis of promising biologically active substances. The analysis of the manifestation of useful properties shows that with the complication of the structure of a substance, its biological activity increases. At the same time, it was noted that at the same time the methods of synthesis of these substances become more complicated, in particular, the processes of obtaining become multistage. In this regard, an urgent topic is the development of accessible methods for obtaining drugs, the improvement of known and the development of new effective, environmentally friendly methods of synthesis. At the moment, a new, little-studied compound is 3,7,10-trioxo2,4,6,8,9,11-hexaaza[3.3.3]propellane (THAP). The aim of the work was to study the process of acetation of 3,7,10-trioxo2,4,6,8,9,11-hexaaza[3.3.3] propellane with acetic anhydride using various acid catalysts (sulfuric, phosphoric and perchloric acids). It was shown that in acetic anhydride there is a partial substitution of protons in the ring NH-groups. A mixture of substances is formed, consisting of di- and triacetyl-substituted THAP. In this case, the formation of the triacetyl derivative proceeds only along two rings, replacing all two NH-group protons in one, and one in the second ring, while the third ring remains not involved in the reaction. It was possible to synthesize 3,7,10-trioxo-2,4,6,8,9,11-hexaacetyl-2,4,6,8,9,11-hexaaza[3.3.3]propellane only by secondary acylation of a mixture of acetyl derivatives THAP with chloride acetyl in an alkaline environment.
Index terms: azapropellans, tricyclic molecules, N-acylation, acetic anhydride, acetyl chloride, acid catalysis


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