6-Aryl- and 6,7-diaryl-1,3-dimethyl-1 H -perimidin-2(3 H )-ones: synthesis, conformational stability, crystal structure and optical properties

6-Bromo- and 6,7-dibromo-1,3-dimethyl-1 -perimidin-2(3 )-ones were arylated with arylboronic acids under Suzuki-Miyaura reaction conditions to afford 6-aryl-, 6-bromo-7-aryl- and 6,7-diaryl-1,3-dimethyl-1 -perimidin-2(3 )-ones. A comparison of the X-ray structural parameters of -diaryl derivatives o...

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Published in:Organic & biomolecular chemistry 2024-12
Main Authors: Dyatlov, Andrey L, Filatova, Ekaterina A, Pozharskii, Alexander F, Marchenko, Sergey S, Demidov, Oleg P, Chernyshev, Anatoly V, Metelitsa, Anatoly V, Brig, Sergei S, Medvedev, Michael G, Bekmansurov, Danis R, Morozov, Pavel G, Gulevskaya, Anna V
Format: Article
Language:English
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Summary:6-Bromo- and 6,7-dibromo-1,3-dimethyl-1 -perimidin-2(3 )-ones were arylated with arylboronic acids under Suzuki-Miyaura reaction conditions to afford 6-aryl-, 6-bromo-7-aryl- and 6,7-diaryl-1,3-dimethyl-1 -perimidin-2(3 )-ones. A comparison of the X-ray structural parameters of -diaryl derivatives of 1,3-dimethyl-1 -perimidin-2(3 )-one, naphthalene and 1,8-bis(dimethylamino)naphthalene (proton sponge) was performed. Based on the data of dynamic H NMR spectroscopy and quantum-chemical calculations, barriers to / -isomerization of 6,7-diaryl-1,3-dimethyl-1 -perimidin-2(3 )-ones were estimated. The optical properties of 6-aryl- and 6,7-diaryl-1,3-dimethyl-1 -perimidin-2(3 )-ones as structural analogs of fluorophoric 6-aryl- and 6,7-diaryl-1,8-naphthalimides were studied.
ISSN:1477-0539