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

被引：0

作者：

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
]}

机构：

[1] Southern Fed Univ, Dept Chem, Zorge Str 7, Rostov Na Donu 344090, Russia

[2] North Caucasus Fed Univ, Dept Chem & Pharm, Pushkin Str 1a, Stavropol 355017, Russia

[3] Southern Fed Univ, Inst Phys & Organ Chem, 194-2 Stachka Ave, Rostov Na Donu 344090, Russia

[4] Lomonosov Moscow State Univ, Leninskie Gory 1-3, Moscow 119991, Russia

[5] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2025年 / 23卷 / 04期

基金：

俄罗斯科学基金会;

关键词：

1,8-DIARYLNAPHTHALENES; ATROPISOMERISM; DICARBOXIMIDES; DERIVATIVES; NMR;

D O I：

10.1039/d4ob01680g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：948 / 959

页数：12

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