Disazo dyes containing pyrazole and indole moieties: Synthesis, characterization, absorption characteristics, theoretical calculations, structural and electronic properties

Atay, Çiğdem Karabacak; Kara, Yesim S.; Gökalp, Merve; Kara, İzzet; Tilki, Tahir; Karcı, Fikret

doi:10.1016/j.molliq.2016.01.031

Cited by 20 publications

(9 citation statements)

References 39 publications

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“…b). [54] The cyclocondensation of bis-heterylmonothio-1,3-diketones (104) with arylhydrazines in EtOH under reflux conditions selectively formed the pyrazole C3regioisomer (105) as shown by Method I. The other regioisomer in which the indole moiety connected to the C5-position of pyrazole (107) was obtained by the treatment of 3-acetylpyridine (102 a) and 2-acetylfuran (102 b) with indolyl-dithioester (103) followed by in situ methyl iodide-mediated methylation and cyclocondensation with arylhydrazines in tert-butanol ( t BuOH) in the presence of potassium tert-butoxide (Method II).…”

Section: Aryl/heteryl-linked Indole-c2 Pyrazole Hybridsmentioning

confidence: 99%

“…Karabacak et al synthesized two new disazo indole dyes (298 a,b) through diazotization of 5-amino-4-arylazo-3-methyl-1H-pyrazoles (296) followed by coupling with 2-methylindole and 2-phenylindole as delineated in Scheme 52. [103,104] Both the diazo dyes were extensively characterized and investigated for their solvatochromic behavior in different solvents.…”

Section: Disazo-linked Indole-c3 Pyrazole Hybridsmentioning

confidence: 99%

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Recent Developments in the Synthesis of Indole‐Pyrazole Hybrids

et al. 2022

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Indole and pyrazole are two important scaffolds in the field of medicinal chemistry. Compounds bearing indole and/or pyrazole moiety have been extensively investigated for a wide range of biological applications. Of them, compounds containing both indole and pyrazole moieties (also termed as indole‐pyrazole hybrids) are of particular interest since synergistic pharmacological activities may be gained comparing to those with each individual pharmacophore. Indole‐pyrazole hybrids can be classified into two general classes of direct‐linked hybrids and spacer‐linked hybrids. For each class, it can be sub‐divided into indole‐C2 pyrazole hybrids, indole‐C3 pyrazole hybrids and indole‐C4/5/6/7 pyrazole hybrids based on the substitution position of pyrazole on the indole moiety. Many types of indole‐pyrazole hybrids have been reported with good antimicrobial, anticancer, antitumor, anti‐inflammatory, anti‐oxidant activities etc. However, no papers have been noted to comprehensively summarize the chemical synthesis of these important indole‐pyrazole hybrids as bioactive compounds except for a few reviews focusing on the synthesis of each individual indole‐ and pyrazole‐containing derivatives. Thus, we here present a comprehensive and updated review focusing on the progress of chemical synthesis of all types of indole‐pyrazole hybrids in order to provide a better understanding of the indole‐pyrazole hybrids to researchers in the fields of synthetic chemistry and to facilitating drug development.

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Section: Aryl/heteryl-linked Indole-c2 Pyrazole Hybridsmentioning

confidence: 99%

Section: Disazo-linked Indole-c3 Pyrazole Hybridsmentioning

confidence: 99%

Recent Developments in the Synthesis of Indole‐Pyrazole Hybrids

et al. 2022

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“…The studies in which pyrazole has been used as a heterocyclic coupling component have grown in importance and are frequently encountered in the literature, especially in recent years. 16,[18][19][20][21][22][23] The fact that the various pyrazole derivatives have been used in pharmacology, agricultural chemistry and the dye industry has resulted in the improvement of new synthetic procedures for the synthesis of these compounds. Condensation of β-enaminonitriles and β-ketoesters with hydrazine is one of the most widely used methods for the synthesis of aminopyrazoles and pyrazolones, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and absorption properties of five new heterocyclic disazo dyes containing pyrazole and pyrazolone and their acute toxicities on the freshwater amphipod Gammarus roeseli

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Sari

2021

Coloration Technology

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In this study, five new heterocyclic disazo dyes containing pyrazole and pyrazolone were synthesised (3a-3e). The synthesised disazo dyes were characterised by elemental analysis and Fourier Transform-infrared and proton nuclear magnetic resonance spectroscopy. The effects of two different solvents upon the absorption ability of the dyes substituted with electron-withdrawing and electron-donating groups were examined in detail. In addition, the acute toxicity of each synthesised azo dye was evaluated using a short-term bioassay with Gammarus roeseli (Crustacea: Amphipoda) for 48 hours. According to the evaluations, the dyes 3a, 3b and 3d were categorised as slightly toxic, and the dyes 3c and 3e as practically non-toxic. Considering the toxicity of the dye 3a, it was determined that the substitution of the electron-withdrawing group in the azo dye resulted in more toxicity, while the substitution of the electrondonating group resulted in less toxicity. It was also found that the presence of the strongly electron-withdrawing group resulted in the azo dye becoming more toxic in comparison with the presence of the weakly electron-withdrawing group, but that the presence of the strongly electron-donating group resulted in the azo dye becoming less toxic in comparison with the presence of the weakly electron-donating group. It is contended that this study is novel and of great importance in terms of synthesising new azo dyes, investigating their absorption properties and assessing their acute toxicities.

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“…Dyestuffs can be classified according to their structure or according to end-use application on a certain substrate [23]. For instance, the disperse dyestuffs are characterized by a variety of chemical structures such as monoazo 1 [24], anthraquinone 2 [25] and disazo 3 [26] structures (Fig. 1) and they are applied on hydrophobic substrates such as polyester fibers.…”

Section: Introductionmentioning

confidence: 99%