Synthesis of Thiazolinone, Aminopyrazole, Pyrazolopyrimidine, and Pyrazolotriazine Derivatives Starting from 1‐Naphthyl‐2‐Cyanoacetamide

Fadda, Ahmed A.; Rabie, Ramy; Etman, H. A.

doi:10.1002/jhet.2669

Cited by 20 publications

(13 citation statements)

References 33 publications

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“…The inhibitors were synthesized in the laboratory according to a previously described experimental procedure 17 . The structure formulas of the examined inhibitors are given in Table 1.…”

Section: Inhibitors and Chemicalsmentioning

confidence: 99%

Corrosion Inhibition of Zinc in Hydrochloric Acid Solution using some organic compounds as Eco-friendly Inhibitors

2019

jcbsc

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The effect of some corrosion inhibitors on the corrosion of Zn in 0.5 M HCl have been investigated by using mass loss (ML), potentiodynamic polarization (PP), electrochemical impedance spectroscopy (EIS) and electrochemical frequency modulation (EFM) techniques. Polarization data clearly indicated that these compounds behaved as mixed type inhibitors. The effect of temperature on corrosion inhibition has been studied; the thermodynamic activation and adsorption parameters were calculated and discussed. EIS have used to investigate the mechanism of corrosion inhibition. The adsorption of these compounds on Zn was found to obey Langmuir adsorption isotherm. The surface morphology of the Zn specimens was evaluated using scanning electron microscope (SEM), Atomic Force Microscopy (AFM) and Fourier transform infrared spectroscopy (FTIR). Quantum chemical calculation was applied to elucidate the adsorption mode of inhibitors molecules onto Zn surface.

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“…The inhibitors were synthesized in the laboratory according to a previously described experimental procedure 17 . The structure formulas of the examined inhibitors are given in Table 1.…”

Section: Inhibitors and Chemicalsmentioning

confidence: 99%

Corrosion Inhibition of Zinc in Hydrochloric Acid Solution using some organic compounds as Eco-friendly Inhibitors

2019

jcbsc

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“…Pyrazolo[3,4- d ][1,2,3]triazines 262 were synthesized by Rabie et al [ 159 ] from the diazotization of 4-( N -arylcarboxamide)-3-( N -phenyl)-3,5-diaminopyrazole derivatives 260 with sodium nitrite which underwent in situ cyclization ( Scheme 71 ).…”

Section: Reviewmentioning

confidence: 99%

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

Aggarwal

Kumar

2018

Beilstein J. Org. Chem.

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The condensation of 5-aminopyrazole with various bielectrophilic moieties results in the formation of pyrazoloazines, an interesting array of fused heterocyclic systems. The development of new synthetic routes towards pyrazoloazines for their biological and medicinal exploration is an attractive area for researchers throughout the world. The present review focuses on various synthetic methods developed in the last decade for the synthesis of differently substituted pyrazoloazines by a broad range of organic reactions by means of 5-aminopyrazole as a precursor. ReviewPyrazole and its derivatives are known to exhibit significant biological and pharmacological activities such as: anticancer [1,2], anti-inflammatory [3,4], antioxidant [5], antibacterial [6][7][8], analgesic [9], antiviral [10,11], antimicrobial [12,13], antifungal [6], antiglycemic [14], antiamoebic [15] and antidepressive [16,17]. Considering the immense biological properties pyrazole is one of the most widely studied nitrogen-containing heterocyclic nuclei. Fused pyrazole derivatives are composed of the pyrazole nucleus attached to other heterocyclic moieties which enable them to exhibit improved pharmacological activities compared to the isolated fragments. These compounds are currently used in several marketed drugs like cartazolate (1), zaleplon (2), sildenafil (3), allopurinol (4), indiplon (5), etazolate (6) etc. (Figure 1). Fused pyrazole derivatives, especially pyrazoloazines have been reported to mimic purine bases, present in DNA and RNA, due to close structural resemblance.In addition to the immense biological potential related to fused pyrazoles, their synthetic potential needs to be reviewed for further improvements and extension of interests. Various efforts have been developed for the synthesis of pyrazole-based fused heterocycles. 5-Aminopyrazoles have been extensively employed as useful synthons in designing and constructing a Beilstein J. Org. Chem. 2018, 14, 203-242. 204 A number of review articles have been published by us and others highlighting the synthetic and biological aspects of 5-aminopyrazoles [26][27][28] as well as on the synthesis of fused pyrazole derivatives [25]. However, a perusal of literature reveals that the importance of 5-aminopyrazoles as synthetic precursors for fused heterocycles has not been reported till now to the best of our knowledge. Recent literature shows resurgence of interest in the chemistry and bioactivity of 5-aminopyrazole derivatives leading to improvements in several already known reactions and syntheses of various fused heterocyclic derivatives with various biological activities. Considering the synthetic importance of 5-aminopyrazoles and synthesis of fused pyrazole derivatives with the need for a more general collection, herein we report an exhaustive overview of the main developments in the last decade in the chemistry of 5-aminopyrazoles for the design and synthesis of fused pyrazoloazines.The typical reactivity of 5-aminopyrazoles 5-Aminopyrazoles are polyfunctional co...

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“…The nucleophilic position C‐2 is more reactive than NH, while the electrophilic site C‐3 is more reactive than position C‐1. Cyanoacetamides (Figure ) are highly reactive polyfunctional substrates for preparing of structurally diverse five and six membered heterocycles including pyrazoles, thiazoles, thiophenes, and pyridines . The latter heterocycles that contain one or two heteroatoms have attracted researchers due to their wide range of biological activities .…”

Section: Introductionmentioning

confidence: 99%

Utilization of 5‐Chloro‐2‐(cyanoacetamido)pyridines in the Synthesis of Biologically Active Heterocyclic Hybrids

et al. 2020

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A simple synthesis for a series of chloropyridine derivatives incorporating heterocyclic hybrids has been accomplished. The key reaction involving employment of 5-chloro-2-(cyanoacetamido)pyridines 3 in the synthesis of chloropyridinyl-pyridone, chloropyridinyl-pyrazole, chloropyridinyl-thiazole and chloropyridinyl-thiophene hybrids. The newly synthesized heterocycles were evaluated for their antioxidant and antibacterial activities against Gram-positive and Gram-negative bacterial strains. 3-Amino-N-(3,5-dichloropyridin-2-yl)-1H-pyrazole-4-carboxamide (12 b) was found to be the most potent compound against Escherichia coli and Staphylococcus aureus exhibiting inhibition percent of 92.3 % and 100 %, respectively, when compared to the standard drug ampicillin. Moreover, compound 12 b displayed the most significant antioxidant activity with percent inhibition 87.8 % which is close to the antioxidant activity of ascorbic acid.

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Synthesis of Thiazolinone, Aminopyrazole, Pyrazolopyrimidine, and Pyrazolotriazine Derivatives Starting from 1‐Naphthyl‐2‐Cyanoacetamide

Cited by 20 publications

References 33 publications

Corrosion Inhibition of Zinc in Hydrochloric Acid Solution using some organic compounds as Eco-friendly Inhibitors

Corrosion Inhibition of Zinc in Hydrochloric Acid Solution using some organic compounds as Eco-friendly Inhibitors

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

Utilization of 5‐Chloro‐2‐(cyanoacetamido)pyridines in the Synthesis of Biologically Active Heterocyclic Hybrids

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