Domino-synthesis and fluorescence properties of 4-cyano-2-oxo-1,2-dihydropyridine-3-carboxamides and 2-oxo-1,2-dihydropyridine-3,4-dicarbonitriles

Abstract

ARTICLE This journal isNon-catalytic conversion of 4-oxoalkane-1,1,2,2-tetracarbonitriles in presence of water leads to the formation of mixture of fluorescent 4-cyano-2-oxo-1,2-dihydropyridine-3-carboxamides and 2-oxo-1,2-dihydropyridine-3,4-dicarbonitriles in equal proportions. This transformation was explained and spectral-luminescent properties were investigated, fluorescence quantum yield was measured.

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

“…The carbonyl group, through the formation of hemiketal ( A ), became a source of a hydroxy group that cyclized regiospecifically to the spatially proximate cyano group and caused the carboxamide formation. CACHE processes are essential for the chemistry of oxonitriles and sometimes can be the reason for unusual quasi-hydrolysis of the cyano group under mild conditions [15,19,23], but it was not mentioned by many authors [28–31]. …”

“…They can be easily prepared from an appropriate ketone and TCNE (Scheme 2). Previously we reported about several ways of heterocyclization thereof [15–23], including the formation of pyran derivatives [20–24]. …”

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.…”

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.…”