A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives

Lokhande, Pradeep D.; Hasanzadeh, Kamal; Konda, Shankaraiah G.

doi:10.5155/eurjchem.2.2.223-228.336

Cited by 17 publications

(11 citation statements)

References 32 publications

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“…Compounds 1 and 2 were prepared by following methods reported elsewhere . Sonication of compound 2 yielded formyl pyrazolyl coumarin 3 , which gave the desired receptors as orange‐colored products ( R1–R5 ) upon microwave irradiation with (un)substituted phenylhydrazine. Spectral data obtained by 1 H‐NMR, 13 C‐NMR, FTIR, and mass spectroscopy are found to be in good agreement with the proposed structures of receptors, R1–R5 .…”

Section: Resultssupporting

confidence: 91%

“…Compounds 1 and 2 were prepared by following methods reported elsewhere [50,51]. Sonication of compound 2 yielded formyl pyrazolyl coumarin 3 [52], which gave the desired receptors as orange-colored products (R1-R5) upon microwave irradiation with (un) substituted phenylhydrazine. Spectral data obtained by observed that only receptor R1 is able to exhibit a strong and immediate change in color from yellow to pink; this change in color as detectable by naked eye is seen to have occurred selectively for fluoride ion at minimum concentration of 0.95 ppm ( Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Vilsmeir formylation carried out by ultrasonic irradiation completed in less time and gave higher yield than conventional stirring method. This protocol proved efficient in terms of less reaction time in comparison to 2.5 to 3 h reported in conventional method .…”

Section: Methodsmentioning

confidence: 99%

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Instantaneous and Selective Bare Eye Detection of Inorganic Fluoride Ion by Coumarin–Pyrazole‐Based Receptors

Jain

Gupta

Agarwal

2017

Journal of Heterocyclic Chem

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A series of rationally designed coumarin–pyrazole‐based scaffolds, equipped with N―H and C―H hydrogen bond donors (R1–R5) and containing various electron‐withdrawing groups at key positions, are synthesized and characterized in order to investigate their inorganic fluoride binding properties in highly competitive media (1:1 DMSO–water). Only one, 3‐{4‐[(2,4‐dinitrophenyl)‐hydrazonomethyl]‐1‐phenyl‐1H‐pyrazol‐3‐yl}‐chromen‐2‐one (R1), of the five compounds synthesized, is found to be capable to selectively detect inorganic fluoride via naked eye amongst other anionic species in aqueous media. Qualitative and spectroscopic studies exhibit that receptor R1 has the potential of showing instantaneous change of color from yellow to pink upon addition of sodium fluoride (0.95 ppm) in aqueous media, at concentration lower than that recommended by World Health Organization (1 ppm). Intensity of color increases with increasing fluoride concentration till 5 ppm, beyond which intensity of color change becomes saturated. This has established the applicability of this receptor for assessment of the level of fluoride in water. Anion binding studies carried out by UV–visible titration portrayed substantial bathochromic peak shift from 410 to 495 nm, upon addition of varying concentrations of aqueous sodium fluoride solution, which has validated the color change. Jobs plot data confirmed 1:1 stoichiometry between R1 and fluoride ion. 1H‐NMR investigation reveals that the deprotonation of N―H hydrogen donor group of receptor R1 and its interaction with fluoride ion is responsible for the observed color change.

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Section: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 99%

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Instantaneous and Selective Bare Eye Detection of Inorganic Fluoride Ion by Coumarin–Pyrazole‐Based Receptors

Jain

Gupta

Agarwal

2017

Journal of Heterocyclic Chem

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“…Lokhande et al used the Vilsmeier-Haack reaction to synthesize carboxaldehyde pyrazoles 101 . Condensation of a hydrazine 102 in the presence of phosphorus oxychloride gives the 4-formyl pyrazole ( Scheme 32 ) [ 40 ].…”

Section: The Main Methods Of Access To the Pyrazole Nucleusmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antipsychotic CDPPB, the anti-obesity drug rimonabant, difenamizole, an analgesic, betazole, a H2-receptor agonist and the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Owing to this diversity in the biological field, this nucleus has attracted the attention of many researchers to study its skeleton chemically and biologically. This review highlights the different synthesis methods and the pharmacological properties of pyrazole derivatives. Studies on the synthesis and biological activity of pyrazole derivatives developed by many scientists around the globe are reported.

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“…It is worthy of note that substances containing a 1H-pyrazole moiety have been described as having potential therapeutic utility, such as antiinflammatory [3][4][5], antidepressant [6,7], antipyretic [8], antibacterial [9][10][11][12][13][14], antifungal [12,15] and antitumoral [16]. Of particular interest is the use of 1H-pyrazoles as synthetic intermediates for preparing cyclopropane [17][18][19] and pyrazole derivatives [1,[20][21][22][23][24][25][26]. 1H-Pyrazoles have usually been prepared by starting from aldehydes or ketones, which have either actual or potential α,β-unsaturation [1,[27][28][29][30][31][32][33][34][35][36][37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and antimicrobial evaluation of 1-((5,3-diaryl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one

et al. 2013

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A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives

Cited by 17 publications

References 32 publications

Instantaneous and Selective Bare Eye Detection of Inorganic Fluoride Ion by Coumarin–Pyrazole‐Based Receptors

Instantaneous and Selective Bare Eye Detection of Inorganic Fluoride Ion by Coumarin–Pyrazole‐Based Receptors

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

Synthesis, characterization and antimicrobial evaluation of 1-((5,3-diaryl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one

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