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
收藏
页码：948 / 959
页数：12
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