Regio-orientation in condensation of aminopyrazoles with 1,3-difunctional reagents: synthesis of new pyrazolo[1,5-a]pyrimidines; pyrazolo[3,4-d]pyridazines and 2,4-dihydropyrano[2,3-c]pyrazoles

Elkholy, Ayat; Al-Qalaf, Fawzia; Elnagdi, Mohamed Hilmy

doi:10.3998/ark.5550190.0009.e14

Cited by 28 publications

(3 citation statements)

References 5 publications

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“…The structures of synthesized compounds were confirmed by a variety of spectroscopic techniques, including 1 H and 13 C NMR, mass spectroscopy, IR, and elemental analysis. Elnagdi et al 6,18–20 reported that the reaction of enaminoni-trile 1 with aromatic diazonium salts affords arylhydrazones 2 , which are readily converted into arylazoaminopyrazoles 3 . Our work wanted to determine if 4-arylazo-2H-pyr- azol-3-ylamine derivatives could be used as precursors to arylazo-pyrazolo[1,5-a]pyrimidin-7-ylamines (and pyrimi-din-7-ones).…”

Section: Resultsmentioning

confidence: 99%

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Green Synthesis, Printing Performance, and Antibacterial Activity of Disperse Dyes Incorporating Arylazopyrazolopyrimidines

Khattab

Elnagdi

Haggaga

et al. 2017

AATCC Journal of Research

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Novel heterocyclic arylazo-disperse dyes containing pyrazolo[1,5-a]pyrimidine structures were prepared via conventional refluxing and microwave heating. Starting from cyanoacetic acid, 4-arylazo-2H-pyrazol-3-ylamine was obtained from a sequence of reactions. This pyrazole intermediate afforded the target arylazo-pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a] pyrimidin-7-ones upon cyclization with 3-piperidinylacrylonitrile, ethyl acetoacetate, ethyl(arylhydrazono)acetoacetates, or (arylhydrazono)propanals. The structures of these compounds were confirmed by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy, infrared (IR) analysis, and elemental analysis. The disperse colorants produced were applied to printing on polyester fabrics to give satisfactory results. All the synthesized products were tested as antimicrobial agents. Most compounds exhibited relatively strong antibacterial activity against a panel of Gram-positive and Gram-negative bacteria.

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Section: Resultsmentioning

confidence: 99%

“…15–17 Arylazopyrazolo[1,5-a]pyrimidines were prepared by condensing aminoarylazopyrazoles with β-bifunctional reagents using methodologies initially established in our laboratories. 18–20…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis, Printing Performance, and Antibacterial Activity of Disperse Dyes Incorporating Arylazopyrazolopyrimidines

Khattab

Elnagdi

Haggaga

et al. 2017

AATCC Journal of Research

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“…Enaminonitriles are important intermediates for the preparation of heterocyclic compounds possessing diverse biological activities. They are of particular interest as very promising reagents for cascade heterocyclization, which will undoubtedly become one of the main approaches to the targeted synthesis of heterocycles in the near future, in the rapidly-rising field of combinatorial chemistry [1]- [3]. Non-steroidal anti-inflammatory drugs (NSAIDs) represent a heterogeneous family of pharmacologically active compounds used to alleviate acute and chronic inflammation, pain and fever.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Some Enaminonitrile Derivatives of Antipyrine as Potential Novel Anti-Inflammatory and Analgesic Agents

Fadda¹,

Elattar²

2015

JBM

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The starting (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carbon-hydrazonoyl dicyanide (2) was used as a key intermediate for the syntheses of novel acyclic enaminonitriles 3-10. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 1 H NMR, 13 C NMR and mass spectra). The anti-inflammatory activity data indicated that many of tested compounds protected rats from carrageenan-induced inflammation, and tested compounds 3, 4, 9 and 10 were the most potent among tested compounds. The analgesic activity was determined by the hot plate test (central analgesic activity) and acetic acid induced writhing assay. The results revealed that compounds 3, 4, 9, and 10 exhibited significant activity. However, compound 10 proved to have better or equivalent activities in comparison to the reference drug.

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Utility of Enaminonitriles in Heterocyclic Synthesis: Synthesis of Some New Azepine, Azocine, and Pyrroldione Derivatives

Fadda

Elattar

2014

Journal of Heterocyclic Chem

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Reactions of enaminonitrile derivative 3 with a variety of reagents lead to the syntheses of novel 1,2,4‐triazepin 7, 1,4‐thiazepinone 9, oxazocines 13, 14, oxadiazocines 15, 16, and pyrroldiones 17, 18, 19, 20, 2122 with the aim to explore the use of this exceptionally reactive enaminonitrile 3 in heterocyclic synthesis. Newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 1H‐NMR, 13C‐NMR, and MS).

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Regio-orientation in condensation of aminopyrazoles with 1,3-difunctional reagents: synthesis of new pyrazolo[1,5-a]pyrimidines; pyrazolo[3,4-d]pyridazines and 2,4-dihydropyrano[2,3-c]pyrazoles

Abstract: Pyrazolo [1,5-a]

Cited by 28 publications

References 5 publications

Green Synthesis, Printing Performance, and Antibacterial Activity of Disperse Dyes Incorporating Arylazopyrazolopyrimidines

Green Synthesis, Printing Performance, and Antibacterial Activity of Disperse Dyes Incorporating Arylazopyrazolopyrimidines

Design and Synthesis of Some Enaminonitrile Derivatives of Antipyrine as Potential Novel Anti-Inflammatory and Analgesic Agents

Utility of Enaminonitriles in Heterocyclic Synthesis: Synthesis of Some New Azepine, Azocine, and Pyrroldione Derivatives

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