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

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

Journal

Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2025, Volume: 23, Pages: 948-959 Pages count : 12 DOI: 10.1039/d4ob01680g

Authors

Dyatlov Andrey L. ¹ , Filatova Ekaterina A. ¹ , Pozharskii Alexander F. ¹ , Marchenko Sergey S. ¹ , Demidov Oleg P. ² , Chernyshev Anatoly V. ³ , Metelitsa Anatoly V. ³ , Brig Sergei S. ^4,5 , Medvedev Michael G. ⁵ , Bekmansurov Danis R. ⁵ , Morozov Pavel G. ¹ , Gulevskaya Anna V. ¹

Affiliations

1	Department of Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation
2	Department of Chemistry and Pharmacy, North Caucasus Federal University, Pushkin str. 1a, 355017 Stavropol, Russian Federation
3	Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka ave., Rostov-on-Don 344090, Russian Federation
4	Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russian Federation
5	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prosp., 47, Moscow, Russian Federation

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.

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. 2025. V.23. P.948-959. DOI: 10.1039/d4ob01680g WOS OpenAlex

Web of science:	WOS:001375188000001
OpenAlex:	W4405111197

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