title: Synthesis of some novel biologically active disperse dyes derived from 4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydro-pyridine-3-carbonitrile as coupling component and their colour assessment on polyester fabrics.
abstract: A series of novel azo-disperse dyes containing alkylhydrazonopyridinone structures were synthesized. 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitrile (8) is synthesized by one-pot synthesis using ethyl cyanoacetate, propylamine, and ethyl acetoacetate. Compound 8 is then coupled with aromatic and heteroaromatic diazonium salts to afford the corresponding aryl- and heteroaryl-4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitriles 12a,b and 13a-c. Structural assignments to the dyes were made using NMR spectroscopic methods. A high temperature dyeing method was employed to apply these dyes to polyester fabrics. Most of the dyed fabrics tested displayed very good light fastness levels and good wash fastness. Finally, the biological activity of the prepared dyes against Gram positive bacteria and Gram negative bacteria were evaluated.
authors: Department of Chemistry, University of Aleppo, Aleppo, Syria.
authors: Samar M
authors: SM
authors: Ashkar
authors: Morsy A
authors: MA
authors: El-Apasery
authors: Marwan M
authors: MM
authors: Touma
authors: Mohamed H
authors: MH
authors: Elnagdi
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D052978:Disk Diffusion Antimicrobial Tests; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: C576551:4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydro-pyridine-3-carbonitrile; D000900:Anti-Bacterial Agents; D004396:Coloring Agents; D006835:Hydrazones; D009570:Nitriles; D011725:Pyridines; D011728:Pyridones