Synthesis and tautomeric structures of some novel thiophene-based bis-heterocyclic monoazo dyes

Abstract

In this study, ethyl 2-amino-5-methyl-4-(phenylcarbamoyl)thiophene-3- carboxylate (1) was prepared using Gewald's methodology. This 2-aminothiophene derivative was diazotised and coupled with, 3-methyl-1H-pyrazolin-5-one, 3-methyl-1-phenylpyrazolin-5-one, 3-amino-5-hydroxy-1H-pyrazole, 3-amino-5-hydroxy-1-phenylpyrazole, 3-cyano-6-hydroxy-4-methyl-2-pyridone, barbituric acid and 4-hydroxycoumarin, respectively (2-8). The newly synthesized bis-heterocyclic monoazo dyes based on thiophene ring were characterised by elemental analysis and spectral methods. The solvatochromic behaviour and tautomeric structures of these bis-heterocyclic monoazo dyes in various solvents was evaluated. Acid and base effects on the visible absorption maxima of the dyes are also reported. © 2012 Elsevier B.V. All rights reserved.