A Concise Review on the Synthesis and Reactions of Pyrazolopyrazine Heterocycles

ul‐Malik, Mokhtar A. Abd; Zaki, Remon M.; El‐Dean, Adel M. Kamal; Radwan, Shaban M.

doi:10.1002/jhet.3225

Cited by 15 publications

(12 citation statements)

References 75 publications

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“…Among the N -heterocycle compounds, pyrazolo[3,4- b ] pyridine scaffold is the valuable scaffold of material drugs and KDR kinase inhibition 53 , 54 . Recent research in material chemistry confirmed that pyrazolo[3,4- b ] pyridine compounds are key intermediates in industry, semiconductors and organic light-emitting diodes 55 .…”

Section: Introductionmentioning

confidence: 99%

Catalytic synthesis of new pyrazolo [3,4-b] pyridine via a cooperative vinylogous anomeric-based oxidation

Sepehrmansourie

Zarei

Zolfigol

et al. 2022

Sci Rep

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In this study, a novel nano-magnetic metal–organic frameworks based on Fe3O4 namely Fe3O4@MIL-101(Cr)-N(CH2PO3)2 was synthesized and fully characterized. The prepared sample was used as catalyst in the synthesis of pyrazolo [3,4-b] pyridines as convenient medicine by condensation reaction of aldehydes, 5-(1H-Indol-3-yl)- 2H-pyrazol-3-ylamine and 3-(cyanoacetyl)indole via a CVABO. The products were obtained with high yields at 100 °C and under solvent-free conditions.

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Section: Introductionmentioning

confidence: 99%

Catalytic synthesis of new pyrazolo [3,4-b] pyridine via a cooperative vinylogous anomeric-based oxidation

Sepehrmansourie

Zarei

Zolfigol

et al. 2022

Sci Rep

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“…For example, in Hoffmann-La Roche directed to effective Bruton's Tyrosine Kinase inhibition the corresponding lead compound (1 f) bearing amine substituent was identified and scaled up for toxicology studies. [7h] The approaches to the synthesis of pyrazolo [1,5-a]pyrazine heterocyclic system (2) were recently reviewed [8] and the main techniques used by medicinal chemists are summarized in Figure 2. Important, that all approaches were based on the annelation of the pyrazine ring to the pyrazole one.…”

Section: Introductionmentioning

confidence: 99%

“…The approaches to the synthesis of pyrazolo[1,5‐a]pyrazine heterocyclic system ( 2 ) were recently reviewed [8] and the main techniques used by medicinal chemists are summarized in Figure 2. Important, that all approaches were based on the annelation of the pyrazine ring to the pyrazole one.…”

Section: Introductionmentioning

confidence: 99%

Straightforward Synthesis of Functionalized 4,5,6,7‐Tetrahydro‐pyrazolo[1,5‐a]pyrazines – Important Building Blocks for Medicinal Chemistry

et al. 2022

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A set of building blocks based on the 4,5,6,7‐tetrahydro‐pyrazolo[1,5‐a]pyrazine scaffold is synthesized in a multigram scale in a cost‐efficient manner. The possibility of the introduction of different substituents, neutral or functionalized in different positions of pyrazole and/or piperazine rings, is shown. The efficacy of using NH‐pyrazole carbonic acids as a key intermediate of the process is demonstrated. The regioselectivity for direct insertion of the substituent to the 4,5,6,7‐tetrahydro‐pyrazolo[1,5‐a]pyrazine core is discussed. The synthetic perspectives for using the functionalized 4,5,6,7‐tetrahydro‐pyrazolo[1,5‐a]pyrazine as a bifunctional scaffold is discussed. The utilizing of building blocks obtained for the different region‐ and/or stereoselective synthesis, including sole transformations or modifications of functional groups, is demonstrated. The advantages of the proposed approach are proven compared with the other known methodologies.

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“…In continuation of our previous work and because of increased interest in pyrazolo[3,4‐ b ]pyrazine moiety, some novel thienopyrazolopyrazines that have not been reported previously were required for the study of antimicrobial and anti‐inflammatory activities.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis, reactions, and biological activities of new thieno and furopyrazolo[3,4‐b]pyrazines and their related heterocycles

Zaki

El‐Dean

Radwan

et al. 2019

J Chinese Chemical Soc

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In the present investigation, a simple and straightforward methodology for the preparation of novel bifunctional thienopyrazolopyrazines 4a-d has been reported. Synthesis of thieno or furopyrazolopyrazines 5a,b,e,f was achieved by the reaction of o-amino-esters 4a,b,e,f with 2,5-dimethoxytetrahydrofuran. The latter pyrrolyl derivatives 5a,b,e,f were used as starting intermediates for the synthesis of new pyrimido, pyrido, and pyrazino heterocycles fused to the thieno or furopyrazolopyrazine moiety. Furthermore, alkaline hydrolysis of the o-amino-ester 4a followed by acidification afforded the corresponding o-amino carboxylic acid 15, which was used as a versatile precursor for the synthesis of other heterocyclic compounds fused to the thienopyrazolopyrazine ring system, namely: pyrimidine, oxazine, oxazepine, and pyridine derivatives 16-23. The chemical structures of the synthesized compounds were confirmed on the basis of elemental and spectral analyses (Fourier-transform infrared spectroscopy [FT-IR], 1 H nuclear magnetic resonance [NMR], and mass spectroscopy [MS] in addition to 13 C NMR for some of them). Moreover, from the biological screening, we found that most of the tested compounds exhibited promising antifungal, antibacterial, and anti-inflammatory activities compared with the corresponding reference drugs. K E Y W O R D S anti-inflammatory activity, antimicrobial activity, pyrazolo[3,4-b]pyrazine, synthesis, thienopyrazolopyrazine 1 2 3 3a 4 4a 5 6 7 7a 8 8a 9 S C H E M E 1 Synthesis of 5-amino-6-substituted 3-methyl-1-phenyl-1H-thieno[3,2-e]pyrazolo[3,4-b]pyrazine compounds 4a-d ZAKI ET AL. 659

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A Concise Review on the Synthesis and Reactions of Pyrazolopyrazine Heterocycles

Cited by 15 publications

References 75 publications

Catalytic synthesis of new pyrazolo [3,4-b] pyridine via a cooperative vinylogous anomeric-based oxidation

Catalytic synthesis of new pyrazolo [3,4-b] pyridine via a cooperative vinylogous anomeric-based oxidation

Straightforward Synthesis of Functionalized 4,5,6,7‐Tetrahydro‐pyrazolo[1,5‐a]pyrazines – Important Building Blocks for Medicinal Chemistry

Efficient synthesis, reactions, and biological activities of new thieno and furopyrazolo[3,4‐b]pyrazines and their related heterocycles

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