Anthrapyridone compounds are valuable fluorescent dyes; they are obtained from 1-aminoanthraquinones by acylation and cyclization [1]. Methods have been described for obtaining N-alkylsubstituted anthrapyridones which include introducing alkyl groups into the initial 1-aminoanthraquinone [2].In this letter, we report the possibility of direct N-alkylation of the pyridone ring of pyridone-containing compounds by reacting alkyl halides (using ethyl bromide as an example) with 1-aminoanthrapyridone (1) in an aqueous alkaline suspension, in the presence of benzyltrimethylammonium chloride as a phase transfer catalyst. Similar results were obtained for alkylation of 1,8-diamino-3,6-dihydrodibenzo[f,l,m,n]-2,9-phenanthroline-2,7dione (2) and 1,7-diamino-3,9-dihydrobenzo[1,2,3-d,e:4,5,6-d'e']diquinoline-2,8-dione (3) using a two-fold excess of the alkyl halides. The corresponding ethyl-substituted compounds 4-6 were also isolated and characterized. N O N H 2 R O N N O N H 2 R N H 2 O R N N O R N H 2 R O NH 2 1, 4 2, 5 3, 6 1-3 R = H, 4-6 R = EtThe IR spectra were recorded on a Specord M-80 in KBr disks; the UV spectra were recorded on an SF-26 spectrophotometer in ethanol. The 1 H NMR spectra were obtained on a Bruker WP-200 (200 MHz) in DMSO-d 6 with TMS as the standard. The course of the reactions and the purity of the compounds were monitored and the R f values were also determined on Silufol UV-254 plates.General Alkylation Procedure. A suspension of 1-aminoanthrapyridone (5 g, 0.02 mol) and benzyltrimethylammonium chloride (0.1 g) in water (50 ml) was heated (~100°C) while gradually adding a 50% sodium hydroxide solution (40 ml). The reaction mixture changed color from yellowish-brown to violet. After a homogeneous mass was obtained, ethyl bromide (0.022 mol) was added and the mixture was heated for another 1.5-5 h (monitored by TLC). After the reaction went to completion, the mixture was cooled down, water (100 ml) was added, and the mixture was neutralized with 3% hydrochloric acid. The crystals that precipitated were filtered out and dried in air and then recrystallized from ethanol. __________________________________________________________________________________________
Multiple-chromophore-containing dyes have been synthesized by azo coupling of twentymembered poly(azomethine) dye 1 and 3-nitro-(2a) or 2,4-dinitrobenzene-1-diazonium tetrafluoroborate (2b) in solvents of various polarity (water, chloroform) in the presence or absence of dibenzo-18-crown-6 as phase transfer catalyst. The dyeing ability of the dyes was investigated as well as spectral and kinetic study of azo coupling was performed. The obtained disperse dyes are suitable for dyeing Nylon and polyester fibers from light reddishbrown to dark brown colors with good uniformity of dyeing as well as light, washing and sublimation fastness.In the recent decades, the interest in disperse dyes containing heterocycles has been grown as indicated by patent literature 1 and other publications 2 . These dyes are commonly considered as environment-friendly products.At present, azo dyes, in particular monoazo dyes, are one of the most frequent synthetic dyes used in various fields of industry and research 3 , due to their flexibility and low cost of the diazotization and azo coupling processes. The synthesis of bis-, tris-and in particular polyazo dyes is complicated or impossible. For this reason azo dyes are used for dyeing from yellow to blue colors in most cases. More deep hues are rare. Therefore, a combination of two or more different colors is used for obtaining deep hues. Hence, the synthesis of aromatic matrixes, capable of giving polyazo dyes, characterized by deep colors seems very interesting and significant.
Azo dyes T 0200 A One-Pot Synthesis of Some Novel Tetrakisazo Disperse Dyes BearingTwenty-Membered Macrocyclic Poly(azomethine). -(LAGVILAVA, I.; MATITAISHVILI, T.; IARDALASHVILI, I.; ELIZBARASHVILI*, E.; Collect.
Fused pyridine derivatives R 0450 Novel Method for N-Alkylation of a Pyridone Ring. -Direct N-alkylation of the pyridone ring of pyridone-containing compounds is achieved under phase-transfer catalysis conditions. -(ELIZBARASHVILI, E. N.; LAGVILAVA, I. V.; SAMSONIYA, S. A.; Chem. Heterocycl. Compd. (N. Y.) 41 (2005) 12, 1543-1544; Georgian Tech. Univ., Tbilisi 380075, Georgia; Eng.) -H. Toeppel 32-181
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