Abstract
This work involves the preparation of some new azo and azo-Schiff compounds derived from benzothiophene, dibenzothiophene, and diamines (1, 5-diaminonaphthalene, and thiocarbohydrazide). Azo compounds of benzothiophene and dibenzothiophene have been prepared using different solvents to enhance the miscibility of the polar aqueous solution of the diazonium salt and the slightly polar benzothiophene and dibenzothiophene. The Schiff’s bases have been synthesized by the condensation reaction of carbonyl compound with the diamines. FT-IR has been used to identify the prepared compounds, whereas 1H-NMR and 13C-NMR were used to identify some others. .
Highlights
Aromatic azo dyes, which are characterized by the functional group (-N=N-), are considered the largest group of organic dyes as they have widespread applications in many areas of textile and medicine [1,2]
3.1 General schemes: The work in this research was according to the following schemes: 3.1.1 Scheme for the preparation of azo dyes of benzothiophene, dibenzothiophene and salicylaldehyde: Volume 14, Issue 1, March 2019, pp. (97-119) ISSN: 1992-0849 (Print), 2616-6801 (Online) 3.1.2 Scheme for the preparation of Schiff’s bases of Thiocarbohydrazide and 1, 5diaminonaphthalene: Volume 14, Issue 1, March 2019, pp. (97-119) ISSN: 1992-0849 (Print), 2616-6801 (Online) 3.1.3 Scheme for the preparation of Schiff’s bases of salicylaladehyde azo dyes with 1,5diaminonaphthalene: The two main reactions used in this research are diazo coupling and Schiff base formation, these two reactions were very important in that they can be exploited to link reactive aromatic molecules
The aromatic molecules containing more than one functional group could be used to synthesize multi-functional larger molecules which may tend to increase their biological activity [22]
Summary
Aromatic azo dyes, which are characterized by the functional group (-N=N-), are considered the largest group of organic dyes as they have widespread applications in many areas of textile and medicine [1,2]. Dyes are normally large aromatic molecules that are consisting of more than one linked ring [4]; the more stable derivatives are containing two aryl groups [5]. Prontosil is an azo dye that acts as an antibacterial drug, it is metabolized in vivo to produce the active amine part (sulfanilamide) [6]. Schiff bases resulted from salicylaldehyde condensation have arouse the researchers' interest because of their ability to act as bidentate ligands for transitional metal ions [7,11]. Studies concerning quantitative structure-antitumor activity relationship of a series of Schiff bases derived from variously substituted aromatic amines and aldehydes, it has been shown that azomethines from salicylaldehydes gave the best correlation [12,13]. The reported biological activity of azo dyes and the pharmacological activity of Schiff bases mentioned above were the motive to conduct this research
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