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In this work, four series of azo thiazole dye derivatives (4a to 4d) have been effectively synthesized using readily available starting materials and applied to color and polish cotton fabrics under supercritical carbon dioxide fluid. The new dyes have been analyzed using elemental analysis and standard spectroscopy methods. They are evaluated for hostility to pseudomonas, Escherichia coli, bacillus cereus, and Staphylococcus aureususing the cup plate strategy at different DMSO concentrations. Remarkable results were obtained for antibacterial activity against Bacillus cereus, Staphylococcus aureus(G+ bacteria), and pseudomonas, Escherichia coli(G− bacteria) compared with selected antibiotics as a reference standard. Five process variables were investigated: pressure, temperature, dye concentration, time, and organic electrolyte concentration. All four dyes demonstrated excellent washing, rubbing, and perspiration fastness (color change and staining grade of 5). Outstanding different color hues and excellent leveling properties were shown on cotton fabric.

The hydrazone 1reacts with DMFDMA to give 2dimethylaminomethylene3phenylhydrazonoindan1one 2which reacts with hydrazine hydrate and the pyrazole derivative 4to afford the indenopyrazole derivatives 3and the indenofluorene 5respectively. The reaction of 2with the active methylene compounds, mainly malononitrile, cyanoacetamide and malononitrile dimer was investigated and found to proceed successfully to yield the indenopyran 7, indenpyridine 8band trinitrile 9respectively. Compound 2reacted with lHbenzimidazole2acetonitrile 10to give to the diazaindenofluorene derivative 11. Also, 2reacted with ωcyano compounds 12a,bto afford the indenopyran 14. On the other hand the hydrazone 1was allowed to react with the enaminones 15, 18and 21affording the diazabenzoazulene derivatives 17, 20and the indeno1,2bpyridin 23, respectively.

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