Abstract
Six azo disperse dyes were prepared by diazotizing 4-amino hippuric acid and coupled with barbituric acid and 2-thiobarbituric acid. Then, the products were reacted with aromatic aldehyde, sodium acetate, and acetic anhydride, and oxazolone derivatives were formed. Characterization of the dyes was carried out by using UV-Vis, FT-IR,1H NMR and13C NMR, and mass spectroscopic techniques. The solvatochromic behavior of azo disperse dyes was evaluated in various solvents. The effects of substituents of aromatic aldehyde, barbiturate, and thiobarbiturate ring on the color of dyes were investigated.
Highlights
It is well known that azo compounds are the most widely class of industrial synthesized organic dyes due to their versatile application in various elds, such as dyeing textile ber, biological-pharmacological activities, and advanced application in organic synthesis [1,2,3]
Most of the heterocyclic dyes are derived from the diazo components consisting of ve-membered rings containing one or more nitrogen heteroatoms, with the rings being fused into another aromatic ring [4]
Barbiturates are a class of drugs that are utilized as anesthetics and sleeping agents and are used for the treatment of anxiety, epilepsy, and other psychiatric disorders and possess effects on the motor and sensory functions [15]. 2- iobarbituric acid is used in the 2-thioxo-2,3-dihydro-4,6(1H,5H)pyrimidinedione pharmacological and analytical elds [16, 17]. erefore, several studies have been published on the synthesis and spectral properties of several azo barbituric acids so far [18,19,20,21,22]
Summary
It is well known that azo compounds are the most widely class of industrial synthesized organic dyes due to their versatile application in various elds, such as dyeing textile ber, biological-pharmacological activities, and advanced application in organic synthesis [1,2,3]. Many heterocyclic compounds are used extensively in disperse dye chemistry for textile or nontextile applications. They are very important in applications such as disperse dyes for polyester bers, reprography, functional dye and nonlinear optical systems, photodynamic therapy, and lasers [5,6,7,8,9,10]. We report the synthesis of a series of new azo dyes based on barbituric acid (Scheme 1). E visible absorption spectra in various solvents of these dyes and effects of substituents of aromatic aldehyde, barbiturate, and thiobarbiturate ring on the color of dyes were discussed
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