Novel bis-(3-cyano-2-pyridones) derivatives: synthesis and fluorescent properties

Abstract

Novel substituted bis-(3-cyano-2-pyridone) derivatives were prepared via a powerful method using enaminonitriles push-pull dienes as key building blocks. The synthesis was performed in three-steps from easily accessible starting materials in good yields. All target products were structurally elucidated by spectroscopic data. The reaction mechanism for formation of bis (3cyano-2-pyridone) derivatives was proposed. The structures of enaminonitriles 3a and bispyridones 4c were confirmed by single-crystal X-ray diffraction. The florescent study of some bis (3-cyano-2-pyridones) derivatives was reported.

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…”

“…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.…”

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

“…The pyridone fragment, in particular, the 2-oxonicotinonitrile one, causes the appearance of fluorescent properties in the molecule [25][26][27][28][29][30][31][32][33][34][35][36]. However, there is practically no information in the literature on the systematic study of the effect of an individual substituent on the photophysical properties of such compounds, despite the fact that the optical properties can be finely tuned by introducing individual functional groups.…”