Synthesis and Spectroscopic Properties of Some New Disazo Dyes Based on 3-Amino-5-Hydroxy-1H-Pyrazole

Abstract

In this study, a new series of 3-amino-5-hydroxy-1H-pyrazole derivative dyes were synthesized and characterized. For this purpose, firstly the m- and o- substituted aniline derivatives were diazotised, the resulting compounds were coupled with 3-amino crotononitrile. 5-amino-4-arylazo-3-methyl-1H-pyrazoles (2a-h) were synthesized by reacting the obtained product (1a-h) with hydrazine monohydrate. Subsequently, the 5-amino-4-arylazo-3-methyl-1H-pyrazoles were diazotised and coupled with 3-amino-5-hydroxy-1H-pyrazole to synthesize 8 new disazo dyes (3a-h). The structure of the eight dyes obtained were determined by various spectrophotometric methods such as Fourier transform infrared spectroscopy (FT-IR), Nuclear magnetic resonance spectroscopy (1H-NMR), Ultraviolet visible region absorption spectroscopy (UV-Vis) and elemental analysis. The maximum absorption wavelengths of the dyes in six different solvents were determined and the acid-base effects on the absorption spectra were investigated. At the end of this study, 8 new aminopyrazole derivative disazo dyes were introduced to the textile and azo dyestuff literature.

Keywords

• Heterocyclic compounds
• Disazo dyes
• Aminopyrazole

3-Amino-5-Hidroksi-1H-Pirazol Bazlı Bazı Yeni Disazo Boyarmaddelerinin Sentezi ve Spektroskopik Özellikleri

Abstract

Bu çalışmada, yeni bir dizi 3-amino-5-hidroksi-1H-pirazol türevi boyarmadde sentezlendi ve karakterize edildi. Bu maksatla, m- ve o- sübstitüe anilin türevleri öncelikle diazolandı, elde edilen bileşikler 3-amino krotononitril ile kenetlendi. Elde edilen ürün (1a-h) hidrazin monohidrat ile etkileştirilerek 5-amino-4-arilazo-3-metil-1H-pirazoller (2a-h) sentezlendi. Sonrasında 5-amino-4-arilazo-3-metil-1H-pirazoller diazolandı ve 3-amino-5-hidroksi-1H-pirazol ile kenetlenerek 8 adet yeni disazo boyarmaddesi (3a-h) sentezlenmiş oldu. Elde edilen sekiz boyarmaddenin yapısı Fourier dönüşümlü infrared spektroskopisi (FT-IR), Nükleer manyetik rezonans spektroskopisi (1H-NMR), Ultraviyole görünür bölge absorpsiyon spektroskopisi (UV-Vis) ve element analizi gibi çeşitli spektrofotometrik yöntemlerle belirlendi. Altı farklı çözücüde boyarmaddelerin maksimum absorpsiyon dalga boyları belirlendi ve absorpsiyon spektrumları üzerine asit-baz etkisi incelendi. Bu çalışma sonunda tekstil ve azo boyarmadde literatürüne 8 adet yeni aminopirazol türevi disazo boyarmaddeleri kazandırıldı.

Keywords

• Heterosiklik bileşikler
• Disazo boyalar
• Aminopirazol

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