Synthesis of some substituted pyrazole-1-carbothioamides and spectral correlations in 3-(3,4-dibromophenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamides

Thirunarayanan, Ganesamoorthy; Sekar, K.

doi:10.5339/connect.2013.18

Cited by 3 publications

(7 citation statements)

References 27 publications

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“…The correlation equations for CO and CN are given in equations (2) 3(ester) protons are presented in Table 4. In nuclear magnetic resonance spectra, the 1 H or the 13 [12-14, 22, 24, 26, 28, 29] are presented in Table 5. The CH 3(keto) proton chemical shifts (δ, ppm) with Hammett σ, σ R constants and R parameters gave satisfactory correlations.…”

Section: Spectral Correlationsmentioning

confidence: 99%

“…The correlation equations for CH 3(keto) , H 4 , H 4 ′, H 5 , CH 2 , OCH 3 and CH 3(ester) proton chemical shifts (δ, ppm) are given in equations (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22). …”

Section: Spectral Correlationsmentioning

confidence: 99%

“…Organic chemists, spectral analysts, and physical organic chemists [12-14, 22, 24, 26, 28, 29] have made extensive study of 13 C NMR spectra for a large number of ketones, styrenes, keto-epoxides and pyrazolines. In their investigation, they assessed the linear correlation of the chemical shifts (ppm) of vinyl, C=N and carbonyl carbons with Hammett σ constants, F and R parameters.…”

Section: C Nmr Spectramentioning

confidence: 99%

“…This spatial arrangement of the protons was confirmed by 1 H NMR and XRD analysis. Many solvent assisted and solvent-free methods including cyclization [15,16], N-acetylation, N-thio-acetylation [17], Nphenylation [15], N-thio-amination [12,13] and condensation [14] were reported in the literature for synthesis of these pyrazoline derivatives. The catalysts such as, Lewis acids, weak acids [18], polyacids [19], sodium acetate [20], clays [21], fly-ash:H 2 SO 4 [14], SiO 2 -H 3 PO 4 [22], preheated fly-ash [12], fly-ash:PTS [13], with or without microwave and ultrasound irradiation [23] were utilized for the above reactions.…”

Section: Introductionmentioning

confidence: 99%

“…The important biological activities of pyrazoline derivatives are anti-bacterial [1], anti-fungal [2], antidepressants [3], anti-convulsant [4], anti-inflammatory [5], anti-tumour [6], anaesthetic [7], analgesic [8], anti-cancer [9], anti-Helicobacter pylori [10], MAO-B inhibitors [11], steroidal, nitric oxide synthase inhibitor, anti-viral and cannabinoid CBI receptor antagonists [5]. They belong to the bi-nitrogen five membered heterocyclic compounds containing three hydrogens in different planes [12][13][14]. This spatial arrangement of the protons was confirmed by 1 H NMR and XRD analysis.…”

Section: Introductionmentioning

confidence: 99%

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Solvent-Free Synthesis and Spectral Correlation of 1N-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazolines

Thirunarayanan¹,

Sekar²

2017

MOCR

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Abstract.A series containing fourteen 1 N-acetyl-3-(4-β-methacrylate)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines were synthesized by KF/Al 2 O 3 catalyzed solvent-free condensation of 1 Nacetyl-3-(4-hydroxyphenyl)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines and (E)-methyl-2-[2-(bromo methyl)-phenyl]-3-methoxyacrylate under microwave irradiation. The yields of the above 1 Nacetyl-3-(4-β-methacrylate)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines were more than 90%. These pyrazolines were characterized by their physical constants, IR, NMR and Mass spectral data. The infrared spectral frequencies (ν, cm -1 ) and NMR chemical shifts (δ, ppm) of proton and carbons of these pyrazolines were assigned and correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses, the effects of substituent on the above spectral data have been discussed.Keywords: Solvent-free synthesis, KF/Al 2 O 3 , β-methacrylate-1 N-acetylpyrazolines, IR spectra, NMR spectra, Hammett correlation IntroductionThe 1 H-4,5-dihydropyrazoline and 1 N-acetyl-4,5-dihydroprazoline derivatives play structurally more important roles in pharmaceutical field of research because they possess numerous biological activities. were utilized for the above reactions. Now-a-days chemists and organic researchers have paid more attention to solvent-free methods. These methods are important and play vital role for synthesis of organics due to easy work-up procedure, technique, shorter time, less hazardousness, less pollution to the environment, higher yield. Sasikala et al.,[15] have synthesised some 5-chloro-2-thienyl based pyrazoline derivatives by solvent-free method and studied the antimicrobial activities. Sakthinathan et al.[20] have synthesised and studied the effects of substituent on 2-naphthyl based pyrazolines. Spectroscopic data were used for prediction of ground state equilibration of organic compounds such as, E, Z or cis-trans isomers of unsaturated compounds such as, alkenes, alkynes, polyenes, enol-enones, unsaturated acid chlorides, ω-halo-acyl compounds and pyrazoline derivatives. These spectroscopic data were applied for the study of spectral linear regression through Hammett equation. Thirunarayanan et al. have studied the effects of substituents and solventfree synthesis of some 5-bromo-2-thienyl based pyrazolines [22]. The solvent-free synthesis and the Modern

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Section: Spectral Correlationsmentioning

confidence: 99%

Section: Spectral Correlationsmentioning

confidence: 99%

Section: C Nmr Spectramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Solvent-Free Synthesis and Spectral Correlation of 1N-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazolines

Thirunarayanan¹,

Sekar²

2017

MOCR

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Pharmacological and Insect Antifeedant Activities of some 3-(2,4-Dichloro-5-Fluorophenyl)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazole-1-Carbothioamides

Thirunarayanan

2014

ILCPA

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A series containing twelve titled compounds were synthesized by solvent-free method and their purities were examined by literature procedure. These compounds were subjected to study the pharmacological effects such as antibacterial, antifungal and antioxidant activities and the insect antifeedant activities using Bauer-Kirby disc diffusion method with their bacterial and fungal strains, DPPH radical scavenging and leaf disc bio-assay method with 4 th instar larvae Achoea janata L. Keywords:Halo aryl 4,5-dihydro-1H-pyrazole-1-carbothioamides; Antibacterial activity, Antifungal activity, Antioxidant activity, insect antifeedant activity INTROUCTIONGenerally, pyrazoline and their derivatives possess important biological activities due to the presence of C=N, N-N and other polar functional groups attached the pyrazoline moiety [1][2] In these derivatives, the formation of pyrazoline ring was confirmed by infrared and NMR spectra. From infrared spectra the cyclic C=N and N-N are the characteristics stretches (ν, cm -1 ) [29]. The protons of the pyrazoline rings are existed in the trans-positions gave

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Pharmacological and Insect Antifeedant Activities of some 3-(2,4-Dichloro-5-Fluorophenyl)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazole-1-Carbothioamides

Thirunarayanan

2014

ILCPA

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Synthesis of some substituted pyrazole-1-carbothioamides and spectral correlations in 3-(3,4-dibromophenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamides

Cited by 3 publications

References 27 publications

Solvent-Free Synthesis and Spectral Correlation of <sup>1</sup><i>N</i>-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-<sup>1</sup><i>H</i>-Pyrazolines

Solvent-Free Synthesis and Spectral Correlation of <sup>1</sup><i>N</i>-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-<sup>1</sup><i>H</i>-Pyrazolines

Pharmacological and Insect Antifeedant Activities of some 3-(2,4-Dichloro-5-Fluorophenyl)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazole-1-Carbothioamides

Pharmacological and Insect Antifeedant Activities of some 3-(2,4-Dichloro-5-Fluorophenyl)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazole-1-Carbothioamides

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