6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties
6-Bromo- and 6,7-dibromo-1,3-dimethyl-1H-perimidin-2(3H)-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-1H-perimidin-2(3H)-ones. A comparison of the X-ray structural parameters of peri-diaryl derivativ...
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2025
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ir-123456789-295992025-02-03T13:52:31Z 6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties Demidov, O. P. Демидов, О. П. Alkylation Crystals structures Isomerization Isomers Naphthalene Synthesis (chemical) Arylboronic acids Conformational stabilities; H NMR spectroscopy Property Proton sponge Reaction conditions Structural parameter Suzuki-Miyaura reaction Nuclear magnetic resonance spectroscopy 6-Bromo- and 6,7-dibromo-1,3-dimethyl-1H-perimidin-2(3H)-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-1H-perimidin-2(3H)-ones. A comparison of the X-ray structural parameters of peri-diaryl derivatives of 1,3-dimethyl-1H-perimidin-2(3H)-one, naphthalene and 1,8-bis(dimethylamino)naphthalene (proton sponge) was performed. Based on the data of dynamic 1H NMR spectroscopy and quantum-chemical calculations, barriers to syn/anti-isomerization of 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones were estimated. The optical properties of 6-aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones as structural analogs of fluorophoric 6-aryl- and 6,7-diaryl-1,8-naphthalimides were studied. 2025-02-03T13:51:07Z 2025-02-03T13:51:07Z 2024 Статья Dyatlov, A.L., Filatova, E.A., Pozharskii, A.F., Marchenko, S.S., Demidov, O.P., Chernyshev, A.V., Metelitsa, A.V., Brig, S.S., Medvedev, M.G., Bekmansurov, D.R., Morozov, P.G., Gulevskaya, A.V. 6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties // Organic and Biomolecular Chemistry. - 2024. - 23 (4). - pp. 948-959. - DOI: 10.1039/d4ob01680g https://dspace.ncfu.ru/handle/123456789/29599 en Organic and Biomolecular Chemistry application/pdf application/pdf Royal Society of Chemistry |
| institution |
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| collection |
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| language |
English |
| topic |
Alkylation Crystals structures Isomerization Isomers Naphthalene Synthesis (chemical) Arylboronic acids Conformational stabilities; H NMR spectroscopy Property Proton sponge Reaction conditions Structural parameter Suzuki-Miyaura reaction Nuclear magnetic resonance spectroscopy |
| spellingShingle |
Alkylation Crystals structures Isomerization Isomers Naphthalene Synthesis (chemical) Arylboronic acids Conformational stabilities; H NMR spectroscopy Property Proton sponge Reaction conditions Structural parameter Suzuki-Miyaura reaction Nuclear magnetic resonance spectroscopy Demidov, O. P. Демидов, О. П. 6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties |
| description |
6-Bromo- and 6,7-dibromo-1,3-dimethyl-1H-perimidin-2(3H)-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-1H-perimidin-2(3H)-ones. A comparison of the X-ray structural parameters of peri-diaryl derivatives of 1,3-dimethyl-1H-perimidin-2(3H)-one, naphthalene and 1,8-bis(dimethylamino)naphthalene (proton sponge) was performed. Based on the data of dynamic 1H NMR spectroscopy and quantum-chemical calculations, barriers to syn/anti-isomerization of 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones were estimated. The optical properties of 6-aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones as structural analogs of fluorophoric 6-aryl- and 6,7-diaryl-1,8-naphthalimides were studied. |
| format |
Статья |
| author |
Demidov, O. P. Демидов, О. П. |
| author_facet |
Demidov, O. P. Демидов, О. П. |
| author_sort |
Demidov, O. P. |
| title |
6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties |
| title_short |
6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties |
| title_full |
6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties |
| title_fullStr |
6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties |
| title_full_unstemmed |
6-Aryl- and 6,7-diaryl-1,3-dimethyl-1H-perimidin-2(3H)-ones: synthesis, conformational stability, crystal structure and optical properties |
| title_sort |
6-aryl- and 6,7-diaryl-1,3-dimethyl-1h-perimidin-2(3h)-ones: synthesis, conformational stability, crystal structure and optical properties |
| publisher |
Royal Society of Chemistry |
| publishDate |
2025 |
| url |
https://dspace.ncfu.ru/handle/123456789/29599 |
| work_keys_str_mv |
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| _version_ |
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