Effect of a Substituent in the Fourth Position on the Optical Properties of 2-Oxonicotinonitriles

Abstract

Based on six representatives of 2-oxonicotinonitriles, the effect of the nature of the substituent in the fourth position of the pyridine system on the photophysical characteristics was studied. The role of the donor/acceptor nature of the substituent and the solvent nature in the absorbing and fluorescent properties of the compounds was shown.

New 2-pyridone-based donor–acceptor dyes: the effect of the donor group position, type of π-linker and acid–base characteristics of the medium on the photophysical properties

“…At first, 6-methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile 8 was obtained from 1,1,1-trifluoropentane-2,4-dione and cyanoacetamide in the presence of diethylamine. 34 Then, pyrrolidine-catalyzed condensation of compound 8 and aromatic aldehydes in 1,4-dioxane followed by acidification of the mixture with 2 M HCl solution led to the desired pyridones 1–5 . The highest yields were achieved using a two- to three-fold excess of pyrrolidine relative to the initial pyridone 8 .…”

Simple and Efficient Synthesis of Highly Functional 2-Oxonicotino­nitriles from 2-Chloronicotinonitriles

“…2-Oxonicotinonitrile derivatives are often characterized by fluorescence in solutions and (or) solid state, including mechanochromic emission. 9 , 12 13 14 15…”

“…For example, previously described compounds 2g – i obtained in a different way, the fluorescence quantum yield reaches 85%. 13 15 Therefore, these studies will be continued with the aim of obtaining a series of pyridones of a similar structure and studying their photophysical properties in order to find effective fluorophores that can be used, for example, as chemosensors.…”

“…2-Oxonicotinonitrile derivatives are often characterized by fluorescence in solutions and (or) solid state, including mechanochromic emission. 9,[12][13][14][15] 2-Oxonicotinonitrile core is the main structural unit in various drugs and constantly attracts the attention of researchers due to its extremely diverse biological properties. There are -amylase and -glucosidase enzyme inhibitors, 16 EGFRWT and EGFRT790M inhibitors, 17 PIM-1/2 kinase inhibitors, 18 Mcl-1 inhibitors, 19 DNA gyrase active inhibitors, 20,21 potential inhibitors against Alzheimer's dis-ease, 4 and anticancer agents with dual VEGFR-2/HER-2 inhibitory activity.…”

Sulfur-Promoted Oxidative Condensation of Chalcones with Unsubstituted Cyanoacetamide in DMSO: Access to 3-Cyanopyrid-2-ones

“…Milrinone D , marketed as Primacor, and Olprinone E exhibit phosphodiesterase inhibitory activity and are used for treating heart failure, particularly when conventional treatment with vasodilators and diuretics is ineffective . Moreover, 3-cyanopyrid-2-one scaffold represents the key feature in many biologically active natural products, such as ricinine F, found in the castor plant with insecticidal and antimalarial activities and could serve as a biomarker of ricin poisoning . In addition, 3-cyanopyrid-2-one derivatives are known for their unique photophysical properties and a wide range of potential applications; for example, G was shown as a fluorescent tag for visualization and an electrochemical sensor for nitrite detection .…”