Synthesis of 5-(3'-Amino-4'-Arylazo-1H-Pyrazol-5'-yl Azo) Barbituric Acid Dyes and Investigation of Spectroscopic Properties

In this study, firstly aniline derivatives were diazotized and then these diazotized compounds were reacted with malononitrile for synthesizing the aril-azo malononitrile compounds (1a-1m). Secondly, 4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by effecting hydrazine monohydrate with aril-azo malononitrile compounds (1a-1m). Finally, the diazonium salts of these compounds were reacted with barbituric acid and 5-(3'-amino-4'-arylazo-1H-pyrazole-5'-yl-azo) barbituric acid compounds (3a-3m) which target compounds were obtained. The structures of (3a-3m) compounds were characterized with AT-IR, 1H-NMR and UV–visible spectroscopy. Thus, it was synthesized 13 novel disperse disazo dyes for the first time which contains both diazo and coupling component heterocyclic structure.

5-(3'-Amino-4'-Arilazo-1H-Pirazol-5'-il Azo) Barbitürik Asit Boyarmaddelerin Sentezi ve Spektroskopik Özelliklerinin Ýncelenmesi

Bu çalýþmada öncelikle anilin türevleri diazolanmýþ ve daha sonra diazolanan bu bileþikler, aril-azo-malononitril (1a-1m) bileþiklerini sentezlemek için malononitril ile reaksiyona sokulmuþtur. Ýkinci olarak 4-arilazo-3,5-diamino-1H-pirazol (2a-2m) türevleri, aril-azo-malononitril (1a-1m) bileþikleri ile hidrazin monohidrat etkileþtirilerek sentezlenmiþtir. Son olarak bu bileþiklerin diazonyum tuzlarý barbitürik asit ile reaksiyona sokulmuþ ve hedef bileþikler olan 5-(3'-amino-4'-arilazo-1H-pirazol-5'-il-azo) barbitürik asit (3a-3m) bileþikleri elde edilmiþtir. 3a-3m bileþiklerinin yapýlarý AT-IR, 1H-NMR ve Ultraviyole–görünür bölge spektroskopisi gibi spektral yöntemlerle karakterize edilmiþtir. Böylece hem diazo hem de kenetlenme bileþeni heterosiklik olan 13 adet yeni pirazol türevi dispers disazo boyarmaddeleri sentezlenmiþtir.