New Azo compounds containing an 1,8-naphthalimide moiety were synthesized from 1, 8-naphthalic anhydride by a reaction with p-phenylenediamine or benzidine to produce 1,8-naphthalimide derivatives (1 or 2), which were converted to diazonium salt derivatives by using sodium nitrite and acetic acid at 0-5 áµ’C. The diazonium salt was subjected to a coupling reaction with different substituted phenol in alkaline media at 0-5 áµ’c to produce azo compound derivatives (3-14).
The New Azo compound derivatives (3-14) were identified by 1H-NMR, 13C-NMR, and FTIR and by measuring characteristic physical properties and specific reactions. Also, the ability of the prepared azo compounds to work as acid-base indicator was investigated, since azo dyes have different and sharp colors in acidic or basic solutions.
Isatin is a heterocyclic nitrogen compound that has attracted much interest in recent years due to its diverse biological and pharmacological activities. It can be used in many medical and biological applications, such as antidiabetic, antibiotic, and anticancer agents. The isatin molecule can also be prepared from different substrates by various methods, such as the methods of Sandmeyer, Stolle, Gassman, Meanwell and Hewawasam and others. On the other hand, the isatin molecule can undergo various chemical reactions, such as oxidation, Friedel-Crafts reaction, ring expansion, aldol condensation, and alkylation reactions. As a result of these reactions, several biologically useful biomolecules are formed, including 2-oxindoles, tryptanthrin, indirubins and others. Therefore, the aim of this review was to provide an overview of the synthetic methods of the isatin molecule and its derivatives and to examine the various chemical reactions it undergoes. In addition, a list of some of the recently documented biological activities of isatin derivatives was compiled, such as antidiabetic, antibacterial, anticancer, and other properties.
New Azo compounds containing of 1,8-naphthalimide moiety had been synthesized from 1,8-naphthalic anhydride by reaction with p-phenylenediamine or benzidine to give 1,8-naphthalimide derivatives [1 or 2], which converted into its diazonium salt derivatives that undergo to coupling reaction with different substituted phenol in alkaline media to produce azo compounds derivatives [3-6]. The prepared compounds had been characterized by measuring some of physical properties (melting point), FTIR, 1HNMR and 13CNMR. Also, absorption spectra (UV-Vis spectrophotometry), fluorescence spectra (Fluorescence spectrophotometry) and quantum yield of prepared azo dyes [3 - 6] had been studied in four different solvents of different polarities (EtOH, dioxane, CHCl3 and DMSO). Also, the photo stability of the dyes [3 - 6] was studied by exposing to the ultraviolet light at room temperature for three hours. Thermal stability of dyes (3 & 4) was studied by TGA / DTG. The prepared dyes [3 - 6] were used for the dyeing of raw cotton dyeing at high temperatures and studying their fastness properties such as washing fastness using standard soap (SDS) and rubbing fastness (wet and dry) under controlled conditions of pressure, speed and moisture.
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