untitled European Journal of Chemistry 5 (1) (2014) 192‐200 European Journal of Chemistry ISSN 2153‐2249 (Print) / ISSN 2153‐2257 (Online)  2014 Eurjchem Publishing ‐ Printed in the USA http://dx.doi.org/10.5155/eurjchem.5.1.192‐200.883 European Journal of Chemistry Journal homepage: www.eurjchem.com Arylazoazines and arylazoazoles as interesting disperse dyes: Recent developments with emphasis on our contribution laboratory outcomes Saleh Mohammed Al‐Mousawi *, Morsy Ahmed El‐Apasery, and Mohamed Hilmy Elnagdi Department of Chemistry, Faculty of Science, Kuwait University, Safat 13060, Kuwait *Corresponding author at: Department of Chemistry, Faculty of Science, Kuwait University, Safat 13060, Kuwait. Tel.: +965.24985547. Fax: +965.24816482. E‐mail address: saleh.almousawi@yahoo.com (S. M. Al‐Mousawi). REVIEW INFORMATION ABSTRACT DOI: 10.5155/eurjchem.5.1.192‐200.883 Received: 23 July 2013 Received in revised form: 04 October 2013 Accepted: 06 October 2013 Online: 31 March 2014 KEYWORDS In this review, we report a survey on the synthesis and application of arylazoazines and arylazoazoles as versatile disperse dyes. Recent reports on the synthesis of arylazonicotinates via condensing arylhydrazonals with active methylene nitriles in acetic acid in presence of ammonium acetate is surveyed. The scope and limitations of this synthetic approach which in some cases afford pyridazinones or arylazonicotinates is defined. Microwave assisted as well as ultra sound assisted synthesis of arylazopyridones as established marketed dyes is also surveyed. Conversion of these arylazopyridones into arylazothienopyridones that can de converted into arylazoisoquinoline derivatives is discussed. Synthesis of arylazopyrazoles and pyrazolopyrimidines via microwave or ultra sound is discussed. The utility of the synthesized compounds as well as antimicrobial disperse dyes and efforts to define their potentialities are also covered. Disperse dyes Arylazoazoles Arylazoazines Polyester fabrics Biological activity Microwave irradiation 1. Introduction Arylazoazines have replaced arylazopyrazoles as disperse monoazo dyes of superior properties. Among these dyes (1‐4) are commercially available (Figure 1) [1‐5]. In recent years, we have placed emphasis on developing efficient syntheses of new substitutes aryl and heteroarylazoazines and azoles as potential antimicrobial dyes emphasizing on utility of green methodologies whenever this was possible. In the following article, we survey these results as well as some recent related work worldwide. This study aims to shed light on the potential of arylazonicotinate, pyrido[3,2,c]cinnolines, pyrido[2,3‐d]pyrimi‐ dinones, arylazopyridones, arylazothienopyridones, arylazo‐ thienopyridazines, arylazopyrazoles and pyrazolopyrimidines as antimicrobial disperse dyes for hydrophobic fibers. Thus, encouraging developing large scale preparations of these products as well as commercial utility in dyeing fabrics having antimicrobial activity. 2. Synthetic approaches to arylazonicotinate, pyrido[3,2,c] cinnolines and pyrido[2,3‐d]pyrimidinones derivatives In 1999, Elnagdi et al. [6] reported that coupling enaminones, 1, with aromatic diazonium salts affords arylhydrazonals, 2, that subsequently condensed with active methylene nitriles to yield pyridazine imines, 3 [7]. However, with the help of X‐ray crystal structure determination as well as 13C NMR data it was realized that the reaction of condensing compound 2 with active methylene nitriles produces either pyridazinones or arylazonicotinates based on the reaction conditions [8,9]. It is believed that the pathways for these processes involve initial reaction of compound 2 with active methylene nitriles to yield the hydrazono‐enone, 4, that then cyclizes to generate the pyran‐imine, 5. In the absence of ammonium ion, compound 5 undergoes a Dimroth type rearrangement to yield compound 7 (Scheme 1) (Table 1) [10,11]. Subsequently, Al‐Mousawi et al. has found that in presence excess amount of ammonium acetate the amino derivative 9 is formed. In case of presence excess amount of ammonium acetate pyran‐imine, 5, is attacked by NH3 ion yielding acyclic amidine 8 that then cyclizes followed by water elimination to yield compound 9 [11‐13]. Previously, it was noted in the literature that in some cases pyridazinones 10 are the reaction products (Figure 2‐4) [14‐19]. In contrast, 3‐oxo‐3‐substituted‐2‐arylhydrazonals react with active methylene nitriles to afford the novel 2,6‐ dihydropyrido[3,2,c]cinnolines, 12. These substances are believed to be formed via a 6π‐electrocyclization reaction of the initially formed arylazo nicotinate 7, that generates the tricyclic intermediate product 11, which then aromatizes to produce the cinnoline derivatives, 12 (Scheme 2) [9,11,12]. Al‐Mousawi et al. / European Journal of Chemistry 5 (1) (2014) 192‐200 193 Table 1. Yields of compounds 3, 7, 9, 10 and 12. Compound R Ar X M.p. (°C) Yield (%) 3a C6H5 C6H4NO2‐p CO2Et 199‐201 74 3b Thien‐2‐yl C6H4NO2‐p CO2Et 170‐172 67 3c Fur‐2‐yl C6H4NO2‐p CO2Et 242‐244 75 7a C6H5 C6H4CH3‐p CO2Et 180‐182 84 7b C6H5 C6H4CH3‐p CONH2 276‐277 85 7c C6H4NO2‐p C6H5 CN 276‐278 85 7d C6H4CH3‐p C6H5 CSNH2 166‐168 72 7e CH3 C6H5 CONH2 300 74 7f C6H5 C6H5 300 95 7g C6H5 C6H5 CN 153 95 7h C6H5 C6H5 CO2Et 188‐190 87 7i C6H5 C6H5 CSNH2 190 98 7j C6H5Ph‐p C6H5 CN 145 95 7k C6H5Ph‐p C6H5 CONHNH2 237 95 7l Thien‐2‐yl C6H5 242 98 7m Fur‐2‐yl C6H5 CN 214 95 7n C6H5Cl‐p C6H5 CO2Et 193‐195 89 7o C6H4OCH3‐p C6H5 CO2Et 174‐176 75 7p Pyrrol‐2‐yl C6H5 CO2Et 202‐204 60 7q Pyrazin‐2‐yl C6H4CH3‐p CO2Et 300 68 7r C6H5 CO2Et 188‐190 56 9a C6H5 C6H4CH3‐p CO2Et 210‐212 81 9b C6H4NO2‐p C6H5 CO2Et 200‐202 80 9c C6H5 C6H4Cl‐p CO2Et 188‐190 68 9d Naphthalene‐2‐yl C6H4Cl‐p CO2Et 89‐90 77 10a C6H4CH3‐p C6H5 CO2Et 108‐110 55 10b C6H4CH3‐p C6H5 CONH2 243‐245 52 10c C6H4CH3‐p C6H5 CN 186‐188 64 10d C6H5Cl‐p C6H5 CONH2 211‐213 70 12a H C6H4NO2‐p CO2Et 148‐150 62 12b H C6H4Cl‐p CO2Et 143‐148 83 12c H C6H4NO2‐p CONH2 195 82 12d H C6H5 150 98 12e C6H5 C6H5 CONH2 230 90 12f C6H5 C6H5 CSNH2 170 95 1‐ Greenish Yellow [37781‐00‐3] [1] 2‐ C.I. Disperse Yellow 241, 128450 [83249‐52‐9] [2] 3‐ C.I. Disperse Yellow 211, 12755 [70528‐90‐4] [3] 4‐ Greenish Yellow [88938‐37‐8] [4] Figure 1. Examples of some commercially available dyes. The formed aminonictinates 9a could be readily converted to ethyl 5‐p‐tolyldiazenyl)‐2‐(aminomethyleneamino)‐6‐phenyl nicotinate 13 via condensation with N,N‐dimethylformamide dimethylacetal (DMFDMA) in presence of ammonium acetate. Furthermore, the reaction of compound 13 with ammonium acetate in presence of acetic acid produces 7‐phenyl‐6‐(p‐tolyldiazenyl)pyrido[2,3‐d]pyrimidin‐4(3H)‐one, 14 (Scheme 3). Compounds 7a‐e, 7p, 7q and 9a‐d were tested as disperse dyes on polyester fabrics, where 7a‐e, and 9a‐c display yellow to brownish‐green hues, in addition with very good washing and perspiration fastness and moderate light fastness [20]. 194 Al‐Mousawi et al. / European Journal of Chemistry 5 (1) (2014) 192‐200 Scheme 1 Figure 2. ORTEP drawing of compound 7a. While 7p, 7q and 9d display yellowish‐orange to dark brown hues, and displayed excellent washing and perspiration fastness and moderate light fastness [21]. The antimicrobial activities of the synthesized dyes were screened against selected bacteria and fungi by the agar well diffusion method and their inhibition zones diameters, given in (Table 2), the tests reveal that all of the tested arylazonicotinates disperse dyes showed positive antimicrobial activities against at least one of the tested microorganisms. All of them showed strong activities (>10 mm inhibition zone) against Staphylococcus aureus. Figure 3. ORTEP drawing of compound 9a. Al‐Mousawi et al. / European Journal of Chemistry 5 (1) (2014) 192‐200 195 Scheme 2 Scheme 3 Figure 4. ORTEP drawing of compound 10a. Two of the dyes 7a and 9a, showed medium activities against Gram negative bacteria. Where most of the dyes showed no activities against the two strains of Gram negative bacteria used in the study. Also the majority of the dyes showed weak to no activities at all with Bacillus subtilis. Only dye 7d showed significant inhibition zone >10 mm, against Candida albican. The other dye that showed medium activities against yeast is 7c while all the other dyes failed to affect the yeast growth. It is of value to mention here that after six days the inhibition zone did not show any difference in the size, yet the zone is not clear which indicates that the dye 9b did not kill the microorganisms, but rather had weakened their growth only, this is in comparison to dye 7a or to ampicillin as reference [20]. Also the inhibition zone diameter data for the disperse dyes 7p, 7q and 9d, given in Table 3, shows that all of the tested dyes showed strong positive antimicrobial activities against at least one of the tested microorganisms. All disperse dyes show strong ability to inhibit the growth of Candida albicans which could be considered as interesting observations which needs further investigation. Disperse dye 9d showed the strongest inhibition zones among the five tested microorganisms, also all of these dyes showed cytotoxic effect even after five days of incubation, there were no growths recorded in the inhibited zone for all five tested microorganisms [21]. 3. Synthetic approaches to arylazopyridones and arylazothienopyridones As has been indicated arylazopyridones are already in the market 1‐4 (Figure 1) and are prepared from pyridones 19a‐q. However, in the last decade, we could develop green syntheses of this pyridones utilizing microwave irradiating mixture of acetoacetic esters 15 and cyanoacetamides 16 as well as sonofication of these mixtures. 196 Al‐Mousawi et al. / European Journal of Chemistry 5 (1) (2014) 192‐200 Table 2. Diameter of the zones of inhibition of the dye 7a‐e, and 9a,b a. Dye no Inhibition zone diameter (Nearest mm) (Mean±SD) B. subtilis S. aureus E. coli P. aeruginosa C. albicans 7a 0.1 ± 0.08 15 ± 0.02 77 ‐ ‐ 7b 0.7 ± 0.13 16 ‐ ‐ 7 ± 0.07 7c ‐ 11 ± 0.87 ‐ ‐ ‐ 7d 0.1 16 ± 0.08 ‐ ‐ 12 ± 0.1 9a ‐ 13 7 7 ± 0.05 ‐ 9b ‐ 10 ± 0.2 ‐ ‐ ‐ Ampicillin b 30 ± 0.05 46 ± 0.7 31 ± 0.14 17 ± 0.07 ‐ Cyloheximide c ‐ a “‐“: no inhibition, SD: Standard deviation. b Ampicillin: Antibacterial (100 mg/mL). c Cycloheximide: Antifungal (100 mg/mL). Table 3. Diameter of the zones of inhibition of the dye 7p, 7q and 9d a. Dye no Inhibition zone diameter (Nearest mm) (Mean±SD) B. subtilis S. aureus E. coli P. aeruginosa C. albicans 7p 0.7±0.7 - 2.9±5.8 - 13.4±0.4 7q 12.4±0.2 12.3±0.3 12.7±0.4 13±0.5 11.6±0.4 9d 12.7±0.2 11.7±0.4 14.7±0.4 16.1±0.5 12.2±0.2 Ampicillin b 15±1 18.4±3.5 18.6±1.3 16.0±0.5 Cyloheximide c ‐ a “‐“: no inhibition, SD: Standard deviation. b Ampicillin: Antibacterial (100 mg/mL). c Cycloheximide: Antifungal (100 mg/mL). The obtained products and their yields are listed in Table 4. Alternately we could also show what mixtures of acetoacetic esters 15, cyanoacetic esters 17 and primary amines 18 gives directly the designed pyridones. However in our hands the multistep approach proved superiors since larger yields are obtained in this way. Practically, 1,2‐dihydro‐6‐hydroxy‐4‐ methyl‐2‐oxo‐3‐pyridine carbonitrile 19o and other 1‐ substituted derivatives have found wide application in the preparation of azo dyes, especially as disperse dyes for synthetic fibres [22‐37]. There are many methods for the synthesis of compounds 19a‐h. Condensation of methyl acetoacetate with appropriate amines and methyl cyanoacetate is one of the common methods [38,39]. Also basic condensation of N‐alkylaceto acetamide with enamino‐β‐ketoesters lead to 2(1H)‐ pyridinones [40]. Another efficient method is heating cyanoacetamide and methyl acetoacetate in a microwave oven [41]. Balalaie et al. [42‐48] have reported an efficient three component condensation of alkyl cyanoacetates, primary amines, and β‐ketoesters with higher yields on the surface of silica gel, montmorillonite K‐10, zeolite, and acidic alumina under microwave irradiation, the obtained products 19a‐h in yields ranging from 91 to 93%. These compounds have two tautomeric forms, and in solution there is a very fast equilibration between them [49]. Sakoma et al. [50] has also reported three component condensations of ethyl cyano acetate, primary amines, and ethyl acetoacetate without catalyst. The yields of the obtained products 19o‐q ranged from 86 to 91%. Pyridones 19a‐q could be readily coupled with aromatic and heteroaromatic diazonium salts affording the corresponding aryl and heteroaromatic azopyridones 21a‐t (Table 4). Sakoma et al. [50] and Ashkar et al. [51] have evaluated 3‐(p‐substituted phenylazo)‐6‐pyridone dyes 21a‐d and 21j‐t as disperse dyes on polyester fabrics in order to examine the influence of substituent on the color of the prepared dyes. Sakoma et al. concluded that the exhaustion of the dyes was very good on polyester fabric with excellent wash and light fastness properties. These dyes, however, are noteworthy in their excellent affinity and intensity of color. Other outstanding characteristics of these dyes are that they give deep and bright hues with level dyeings. The bright hue might be attributed to the high planarity of the pyridone ring, because of the lower steric interaction of a five membered ring. The remarkable degree of levelness and brightness after washing is indicative of good penetration and the excellent exhaustion of these dyes for the polyester fabric due to the accumulation of polar groups [50]. As anticipated the aryl and heteroaromatic azopyridones 21e‐i reacted with elemental sulphur either under heating with microwave or by using ultra sound or by conventional heating to yield the corresponding aminothienopyridinones 22a‐e. Trials to develop condensed arylazopyridones have been made by Al‐Mousawi et al. [52] and Al‐Zaydi et al. [53]. Thus Al‐Mousawi reported that reaction of compound 22d with dimethyl acetylenedicarboxylate afforded arylazoisoquinoline, 24, while Al‐Zaydi et al. reported that compound 22e under‐ goes cycloaddition to acrylonitrile yielding isoquinolines, 26. However, up to date, no trial to test potential utility of the isoquinolines 22 and 26 as unique disperse dyes has been made (Scheme 4). 4. Synthetic approaches to arylazothienopyridazines Other class of arylazoazines has also been synthesized by Al‐Mousawi et al. [54‐56]. Thus arylazopyridazinone 27 reacted with DMFDMA affording dihydropyridazine‐4‐ carbonitrile 28 that was readily converted into the pyrido[3,4‐ d]pyridazine‐4,5‐diones 29 on treatment with ammonium acetate and acetic acid. Compound 27 readily reacted with elemental sulphur in the presence of few drops of piperidine yielding arylazoaminothienopyridazine 30 (Scheme 5) (Figure 5) [55]. Typical to the established behaviour of thieno pyridazines compounds, compound 30 reacted with N‐phenyl maleimide in a mixture of acetic acid and dioxane to yield pyrrolo[3,4‐g]phthalazine 33 via intermediary of [4+2] cycloadducts 32. Reaction of compound 30 with DMFDMA afforded the corresponding amidine 34 (Figure 6) [56]. Upon heating compound 34 with ammonium acetate in presence of few drops of acetic acid affords the pyridopyridazine 37 via intermediary of [4+2] cycloadducts 36. Acylating of compound 30 in acetic acid resulted in the formation of acetylamino 35. Again up to date no trial to test potential utility of these compounds 27‐37 as unique disperse dyes has been made. 5. Synthetic approaches to arylazopyrazoles and pyrazolo pyrimidines Elnagdi et al. have, in the seventies, described efficient syntheses of compounds 38 and 39. Al‐Mousawi et al. / European Journal of Chemistry 5 (1) (2014) 192‐200 197 Table 4. Yields of Compounds 19a‐n, 21a‐i, 22a‐e, 24 and 26. Compound R1 R2 R3 X Ar M.p. (°C) Yield (%) 19a CH3 CH3 CH3 H ‐ 285 93 19b C2H5 C2H5 CH3 H ‐ 285 91 19c C2H5 CH3 CH3 H ‐ 285 91 19d CH3 C2H5 CH3 H ‐ 285 91 19e CH3 CH3 C2H5 H ‐ 245 93 19f C2H5 C2H5 C2H5 H ‐ 245 93 19g C2H5 CH3 C2H5 H ‐ 245 94 19h CH3 C2H5 C2H5 H ‐ 245 94 19i ‐ C2H5 C6H5CH2 CH3 ‐ 229‐231 89 19j ‐ C2H5 C2H5 CH3 ‐ 219‐220 88 19k ‐ C2H5 C6H5CH2 H ‐ 250‐252 90 19l C2H5 C2H5 C4H9 H ‐ 254 90 19m C2H5 C2H5 C5H11 H ‐ 126 92 19n C2H5 C2H5 C3H7 H ‐ 218‐220 82 19o C2H5 C2H5 H H ‐ 203 91 19p C2H5 C2H5 CH3 H ‐ 296.5 86 19q C2H5 C2H5 C2H5 H ‐ 178 90 21a ‐ ‐ C3H7 H C6H4OH‐p 252‐255 88 21b ‐ ‐ C3H7 H C6H4CH3‐p 215‐218 86 21c ‐ ‐ C3H7 H 210 65 21d ‐ ‐ C3H7 H 266‐268 80 21e ‐ ‐ C6H5CH2 CH3 C6H5 222‐223 92 21f ‐ ‐ C2H5 CH3 C6H4OCH3‐p 226‐228 92 21g ‐ ‐ C2H5 CH3 C6H5 207‐209 88 21h ‐ ‐ C6H5CH2 H C6H5 239‐240 90 21i ‐ ‐ C4H9 H C6H4CN‐o 206 89 21j ‐ ‐ H H C6H5 200‐203 60.83 21k ‐ ‐ H H C6H4SO3H‐p 198‐201 74.62 21l ‐ ‐ H H C6H4OCH3‐p 158‐161 62.33 21m ‐ ‐ H H C6H4OCH3‐p 218‐221 64.68 21n ‐ ‐ H H C6H4Cl‐p 207‐210 75.57 21o ‐ ‐ CH3 H C6H5 199‐201 42.03 21p ‐ ‐ CH3 H C6H4SO3H‐p 158‐160 90.46 21q ‐ ‐ CH3 H C6H4COOH‐p 158‐160 74.03 21r ‐ ‐ CH3 H C6H4OCH3‐p 143‐145 82.54 21s ‐ ‐ CH3 H C6H4Cl‐p 172‐173 65.05 21t ‐ ‐ CH3 H C6H4OH‐p 178‐180 35.88 22a ‐ ‐ C6H5CH2 CH3 C6H5 280‐282 80 22b ‐ ‐ C2H5 CH3 C6H4OCH3‐p 245‐246 85 22c ‐ ‐ C2H5 CH3 C6H5 241‐243 80 22d ‐ ‐ C6H5CH2 H C6H5 180‐182 78 22e ‐ ‐ C4H9 H C6H4CN‐o 263 95 24 ‐ ‐ ‐ ‐ ‐ 262‐264 66 26 ‐ ‐ ‐ ‐ ‐ 300 70 Scheme 4 198 Al‐Mousawi et al. / European Journal of Chemistry 5 (1) (2014) 192‐200 Scheme 5 Figure 5. ORTEP drawing of compound 30. Compound 38 was patented as dye for keratin fibers and compound 39 was patented by L'Oreal and other companies as constituent of a hair dye formulation. Moreover the biological activity of compound 38 has initially been patented by a Chinese group then published in Journal of Medicinal Chemistry in 2004 [57]. This information prompted us to continue investigating the potential utility of derivatives of both systems as antimicrobial dyes. Thus compound 42 was synthesized utilizing the approach similar to those utilized by Elnagdi et al. [58,59]. Figure 6. ORTEP drawing of compound 34. Al‐Mousawi et al. / European Journal of Chemistry 5 (1) (2014) 192‐200 199 Table 5. Yields of compounds 41, 42, 44, 46, 48, 50, 52 and 54. Compound Ar Ar1 Ar2 M.p. (°C) Yield (%) 41a C6H5 ‐ ‐ 134‐136 74 41b C6H4Cl‐p ‐ ‐ 183‐185 81 41c C6H4NO2‐p ‐ ‐ 140‐142 92 41d C6H4NHCOCH3‐p ‐ ‐ 215‐217 78 42a C6H5 ‐ ‐ 260‐262 54 42b C6H4Cl‐p ‐ ‐ 270‐270 57 42c C6H4NO2‐p ‐ ‐ 255‐257 60 42d C6H4OH‐p ‐ ‐ 245‐246 ‐ 42e C6H4NHCOCH3‐p ‐ ‐ 268‐270 70 44 C6H4OH‐p ‐ ‐ 287‐288 77 46 C6H4OH‐p ‐ ‐ 248‐249 70 48a C6H4OH‐p C6H5 ‐ 301‐302 76 48b C6H4OH‐p C6H4CH3‐p ‐ 309‐310 84 48c C6H4OH‐p C6H4Cl‐p ‐ 306‐307 78 48d C6H4OH‐p Fur‐2‐yl ‐ 292‐293 80 48e C6H4OH‐p Thien‐2‐yl ‐ 276‐277 80 50a C6H4NHCOCH3‐p C6H4Cl‐o ‐ 310‐312 75 50b C6H4NHCOCH3‐p C6H4F‐p ‐ 320‐322 75 50c C6H4NHCOCH3‐p C6H4OCH3‐p ‐ 240‐242 85 52a C6H4NHCOCH3‐p C6H4Cl‐p ‐ 330‐331 72 52b C6H4NHCOCH3‐p C6H4F‐p ‐ 308‐309 73 52c C6H4NHCOCH3‐p C6H4OCH3‐p ‐ 302‐304 79 52d C6H4NHCOCH3‐p C6H3OCH3‐p ‐ 297‐199 74 54a C6H4NHCOCH3‐p C6H5 C6H4OCH3‐p 320‐322 80 54b C6H4NHCOCH3‐p C6H4Br‐p C6H5 220‐222 80 54c C6H4NHCOCH3‐p C6H4Br‐p C6H4Br‐p 308‐310 75 Scheme 6 Some other researchers [60‐63] reported that coupling malononitrile 40 with aryldiazonium chloride afforded arylazomalononitriles, 41, that subsequently condensed with hydrazine hydrate to yield 4‐arylazo‐3,5‐diaminopyrazoles, 42. Al‐Etaibi et al. [62] has converted compounds 42 into a variety of pyrazolo(1,5‐a]pyrimidines 44, 46 and 48a‐e via 200 Al‐Mousawi et al. / European Journal of Chemistry 5 (1) (2014) 192‐200 condensation with 1,3‐diketones 43, enaminonitriles 45, and enaminones 47 (Scheme 6). Sayed et al. [63] has also converted compounds 42 into pyrazolo(1,5‐a]pyrimidines 50a‐c, 52a‐d and 54a‐c, however the structures of the products of addition of ethyl α‐cyano cinnamate derivatives 49, arylidenemalononitrile 51 as well as reaction with chalcones 53 need confirmation as it contradicts with all reported data on similar systems. Although it was difficult in the past, now with availability of 2D NMR and ease of producing X‐rays such structures can be readily confirmed. The synthesized dyes 42a,b, 44, 46, 48a‐d, 50a‐c, 52a‐d and 54a‐c (Table 5) were applied successfully using high temperature dyeing method and obtained solid shades on polyester fabrics with satisfactory levelness of dyeing and depth of shades, the observed hues ranging from yellow to reddish‐violet. The results of fastness properties showed in most cases acceptable to good fastness to light and washing fastness on the polyester fabrics. The antimicrobial activity of dyes 50a‐c, 52a‐d and 54a‐c was also evaluated. 6. Conclusion We have surveyed recently reported syntheses and dye characteristics of arylazonicotinates, arylazopyridones, arylazo pyridazinone as well as arylazopyrazoles emphasizing their promising potential as disperse dyes for polyester fabrics in the light of successful efforts that made their syntheses both environmentally green and economical methodologies as well as established antimicrobial activities of several newly synthesized dyes. 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