Synthesis of azo pyridone dyes

Abstract

Over 50% of all colorants which are used nowdays are azo dyes and pigments, and among them arylazo pyridone dyes (and pigments) have became of interest in last several decades due to the high molar extinction coefficient, and the medium to high light and wet fastness properties. They find application generally as disperse dyes. The importance of disperse dyes increased in the 1970s and 1980s due to the use of polyester and nylon as the main synthetic fibers. Also, disperse dyes were used rapidly since 1970 in inks for the heat-transfer printing of polyester. The main synthetic route for the preparation of azo dyes is coupling reaction between an aromatic diazo compound and a coupling component. Of all dyes manufactured, about 60% are produced by this reaction. Arylazo pyridone dyes can be prepared from pyridone moiety as a coupling component, where substituent can be on nitrogen, and diazonim salts which can be derived from different substituted anilines or other heterocyclic derivatives. In addition, arylazo dyes containing pyridone ring can be prepared from arylazo diketones or arylazo ketoesters (obtained by coupling β-diketones or β-ketoesters with diazonim salts) by condensation with cyanoacetamide. Disazo dyes can be prepared by tetrazotizing a dianiline and coupling it with a pyridone or by diazotizing aniline and coupling it with a dipyridone. Trisazo dyes can be also prepared by diazotizing of aniline and coupling it with a tripyridone or by hexazotizing a trianiline and coupling it with a pyridone. The main goal of this paper is to give a brief review on the synthesis of arylazo pyridone dyes due to the lack of such reviews. In addition, some properties of arylazo pyridone dyes as light fastness and azo-hydrazon tautomerism are disccused

Solvatochromism and quantum mechanical investigation of disazo pyridone dye

“…They were characterised by a high molar extinction coefficient as well as medium‐to‐high light and wet fastness properties . Arylazo pyridone dyes can be also used in the production of colour filters and printing inks .…”

Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study

“…(1) and (2). The LSER concepts developed by Kamlet and Taft and Catalán are some of the most successfully used for quantitative treatments of solvation effects [48].…”

“…They can possess antibacterial, antifungal, anti-inflammatory, antiviral, antitumor and antiplatelet properties [1]. In addition, they are used in the manufacturing of paints, pigments, additives for fuels and lubricants, acid-base indicators, stabilizers for polymers and coatings [2]. Many medications containing 2-pyridone structure are cardiotonics: Milrinone and Amrinone; antibiotics: Pilicides and Curlicides, and antiepileptic: Perampanel [1].…”

“…(2) which qualitatively and quantitatively interprets the effect of solvent dipolarity, polarizability and solvent-solute hydrogen bonding interactions according to Eq. (2):…”

An Eco-Friendly Technique: Solvent-Free Microwave Synthesis and Docking Studies of Some New Pyridine Nucleosides and Their Pharmacological Significance

“…In recent decades, pyridine analogues have been identified as a cornerstone in medicinal chemistry, showing diverse pharmacological actions such as antibacterial [1,2], antifungal [3], anti-inflammatory [4], antiviral [5,6], antitumor [7], and antiplatelet [8,9] properties. In addition, 2-pyridone derivatives are utilized in the production of paints [10], pigments, acid–base indicators, stabilizers for polymers and coatings, and additives for fuels and lubricants [11]. Various pyridine nucleosides have been outlined to have important biological properties [12].…”