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

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

doi:10.1039/D4OB01680G

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

Andrey L. Dyatlov,^a Ekaterina A. Filatova,

^a Alexander F. Pozharskii,

^a Sergey S. Marchenko,^a Oleg P. Demidov,

^b Anatoly V. Chernyshev,

^c Anatoly V. Metelitsa,

^c Sergei S. Brig,^de Michael G. Medvedev,^e Danis R. Bekmansurov,^e Pavel G. Morozov^a and Anna V. Gulevskaya

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation
E-mail: agulevskaya@sfedu.ru

^b Department of Chemistry and Pharmacy, North Caucasus Federal University, Pushkin str. 1a, 355017 Stavropol, Russian Federation

^c Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka ave., Rostov-on-Don 344090, Russian Federation

^d Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russian Federation

^e N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prosp., 47, Moscow, Russian Federation

Abstract

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.

Organic & Biomolecular Chemistry

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

Abstract

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

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