| DOI: | 10.25699/SSSB.2020.33.5.013 |  |
Download PDF |
A STUDY OF SOME STAGES IN SYNTHESIS OF 3,7,10-TRIOXO-2,4,6,8,9,11-HEXAAZA[3.3.3]PROPELLANE
- А.А. Sinitsyna, S.G. Ilyasov
Issues
- Abstract: Here we discuss the most important stages in the synthesis of one of the most promising polycyclic heteroatomic compounds, 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane (ТНАР). Because ТНАР structurally bears six nitrogen atoms and has a close packing, it is a potential compound for the design of chemical entities with a high energy. The key starting compound in the synthesis of ТНАР is 1,5-diaminoglycouril, which in turn is derived via the oxidation of uric acid by sodium persulfate or potassium ferrocyanide. In this study, we expanded a series of oxidizers to transform uric acid into 1,5- diaminoglycouril by potassium permanganate or manganese (IV) oxide. It was found that 1,5-diaminoglycouril was formed in a 29% yield when equimolar portions of uric acid and KMnO4 were used, while the yield of 1,5-diaminoglycouril was 38% when MnO2 was utilized in tenfold excess. Another equally critical stage is the formation of the tertiary ring from 1,5-diaminoglycouril with NH-protected groups. N,Ndimethylaminopyridine was found to have the greatest impact on the synthesis of 3,7,10-trioxo-2,4,6,8,9,11-hexa-bос-2,4,6,8,9,11- hexa[3.3.3]propellane. The highest yield of 3,7,10-trioxo-2,4,6,8,9,11-hexa-bос-2,4,6,8,9,11-hexa[3.3.3]propellane (69%) was achieved when the molar ratio of 1,5-1,5-diaminoglycouril to N,N-dimethylaminopyridine was 8:1 mol/mol. In this case, there was no need for the extraction of the target product from the reaction mass, as product settled down. In addition, mechanochemical activation without solvents was performed for the first time for the synthesis of 3,7,10-trioxo-2,4,6,8,9,11-hexa-bос-2,4,6,8,9,11- hexa[3.3.3]propellane.
- Index terms: Uric acid, oxidation, cyclization, azapropellanes.
Contacts
Russia, 659305, Altai region, Biysk,
Trofimova Street, 27, room 404B
Tel. + 7-923-162-93-27
(executive secretary -
Golykh Roman Nikolayevich)
e-mail: info@s-sibsb.ru
The certificate
