Synthesis of Polysubstituted Pyrazolo[3,4‐<i>b</i>]pyridine‐3‐Carbohydrazide and Pyrazolo[3,4‐<i>d</i>]pyridazine Derivatives

Bhavsar, Dinesh C.; Nikam, Prashant S.; Gangurde, Sachin A.; Toche, Raghunath B.

doi:10.1002/jhet.1779

Cited by 13 publications

(3 citation statements)

References 17 publications

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“…Bhavsar et al . also described the synthesis of substituted pyrazolo[3,4‐ b ]pyridines ( 81 ) from 5‐amino‐4‐formyl pyrazole‐3‐carboxylate ( 80 ) via piperidine assisted condensation and successive intramolecular cyclisation with malononitrile . The ester functionality at C‐3 of 80 reacted smoothly with hydrazines in the presence of piperidine to afford C‐3 substituted pyrazolo[3,4‐ b ]pyridines ( 82 ) as illustrated in Scheme .…”

Section: Synthesis and Applications Of Ethyl 4‐formyl‐1‐aryl‐1h‐pyrazmentioning

confidence: 99%

4‐Formyl‐Pyrazole‐3‐Carboxylate: A Useful Aldo‐X Bifunctional Precursor for the Syntheses of Pyrazole‐fused/Substituted Frameworks

Devi

Shankar

Singh

2017

Journal of Heterocyclic Chem

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Pyrazole, a privileged class of heterocyclic compounds, constitute an interesting template for medicinal chemistry and is represented by several commercial drugs like Sildenafil, Zometapin, Celebrex, and Rimonabant. The presence of two functionalities with different reactivity in pyrazole moiety may open new avenues for insertion of diversity in pyrazole frameworks which may be of high medicinal significance. Ethyl 4‐formyl‐1H‐pyrazole‐3‐carboxylate is a potential Aldo‐X bifunctional building block (AXB3) which may be explored for generating complex pyrazole based molecular frameworks by using various organic transformations. The present manuscript is assimilation of literature pertaining to the synthesis and application of ethyl 4‐formyl‐1H‐pyrazole‐3‐carboxylates and similar AXB3 for the development of pyrazole substituted and fused derivatives.

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Section: Synthesis and Applications Of Ethyl 4‐formyl‐1‐aryl‐1h‐pyrazmentioning

confidence: 99%

4‐Formyl‐Pyrazole‐3‐Carboxylate: A Useful Aldo‐X Bifunctional Precursor for the Syntheses of Pyrazole‐fused/Substituted Frameworks

Devi

Shankar

Singh

2017

Journal of Heterocyclic Chem

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“…Some of them have also inhibitory activities against fibroblast growth factor receptor kinase , TNF‐α , IL‐6 , CDK1 , and glycogen synthase kinase‐3 . A number of methods have already been proposed for the synthesis of pyrazolo[3,4‐ b ] pyridines starting from pyrazole or pyridine moiety .…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of New 6‐Alkylamino‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitrile Derivatives

Dorostkar-Ahmadi

Davoodnia

Tavakoli‐Hoseini

et al. 2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Some new derivatives of 6-alkylamino-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile have been prepared through a Knoevenagel condensation reaction of 5-chloro-1,3-diphenyl-1H-pyrazole-4-carbaldehyde with malononitrile in ethanol containing a few drops of glacial acetic acid at reflux temperature followed by cyclization with primary alkyl amines in the presence of 1,8-diazabicyclo[5.4.0] undec-7-ene as catalyst in refluxing ethanol. The products were characterized on the basis of IR, 1 H NMR, and 13 C NMR spectral and microanalytical data. The 1 H NMR data ruled out the formation of the alternative cyclized isomers 6-imino-7-alkyl-1,3-diphenyl-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles.

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“…Moreover, in spite of their significances pyrazolo[3,4- b ]quinoline derivatives have been less explored as precursors for further transformations. To the best of our knowledge these compounds have been used in the Vilsmeier–Haack formylation reaction and for the synthesis of bispyrazolo[3,4- b :4,3- f ]quinolines and pyrazolo[3,4- b ]quinoline ribofuranosides . Further, the analogous derivatives have been used to synthesize quinoxaline-fused benzo[ h ]isoxazolo[5,4- b ]quinolines and benzo[ a ]pyrazolo[4′,3′:5,6]pyrido-[2,3- c ]phenazine .…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Dipolar Cycloaddition Strategy: Combinatorial Synthesis of Novel Spiro-Tethered Pyrazolo[3,4-b]quinoline Hybrid Heterocycles

et al. 2016

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Synthesis of Polysubstituted Pyrazolo[3,4‐b]pyridine‐3‐Carbohydrazide and Pyrazolo[3,4‐d]pyridazine Derivatives

Cited by 13 publications

References 17 publications

4‐Formyl‐Pyrazole‐3‐Carboxylate: A Useful Aldo‐X Bifunctional Precursor for the Syntheses of Pyrazole‐fused/Substituted Frameworks

4‐Formyl‐Pyrazole‐3‐Carboxylate: A Useful Aldo‐X Bifunctional Precursor for the Syntheses of Pyrazole‐fused/Substituted Frameworks

Facile Synthesis of New 6‐Alkylamino‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitrile Derivatives

Multicomponent Dipolar Cycloaddition Strategy: Combinatorial Synthesis of Novel Spiro-Tethered Pyrazolo[3,4-b]quinoline Hybrid Heterocycles

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