Journal of Siberian Federal University. Chemistry / Synthesis of 4,10-di(2-(1,3-dioxoisoindolin-2-yl)acetyl)-2,6,8,12- tetraacetyl-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane

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Issue
Journal of Siberian Federal University. Chemistry. 2026 19 (3)
Authors
Balakhnina, Maria V.; Balakhnin, Yuriy A.; Kulagina, Daria A.; Sysolyatin, Sergey V.
Contact information
Balakhnina, Maria V.: Institute for Problems of Chemical and Energetic Technologies of the Siberian Branch of the RAS (Biysk, Russian Federation); ; Balakhnin, Yuriy A.:; Kulagina, Daria A. :; Sysolyatin, Sergey V.:
Keywords
glycine; phthalimidoacetic acid; hexaazaisowurtzitane; acylation
Abstract

In the present work, the synthesis of a novel compound, 4,10-di(2-(1,3-dioxoisoindolin-2-yl) acetyl)-2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane, has been accomplished for the first time. The synthesis was carried out by acylation of tetraacetylhexaazaisowurtzitane with N-phthalimidoacetic acid chloride in acetonitrile, followed by recrystallization from dichloroethane, giving a yield of 68.6 % and a purity of 99.2 % according to HPLC data. The structure of the compound was confirmed by IR and NMR (1H, 13C) spectroscopy, and its composition was verified by elemental analysis. The spectral data unambiguously indicate complete acylation of the nitrogen atoms at positions 4 and 10 of the polycyclic framework and the absence of impurities from unreacted hydroxy or amino groups. The solubility of the compound in a wide range of solvents was studied. The obtained results expand the range of tetraacetylhexaazaisowurtzitane derivatives and open up prospects for subsequent pharmacological screening

Pages
478–485
EDN
RFBBBN
Paper at repository of SibFU
https://elib.sfu-kras.ru/handle/2311/160137