Base-catalyzed one-pot tandem reaction: an effective strategy for the synthesis of pyrazolo[3,4-d]pyrimidinone derivatives

Liu, Mingxing; Li, Jiarong; Zheng, Kai; Yao, Huan; Zhang, Qi; Shi, Daxin

doi:10.1016/j.tet.2015.07.065

Cited by 10 publications

(4 citation statements)

References 34 publications

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“…Based on our previous studies, [ 17 ] pyrazolopyrimidinone skeleton 1 was rapidly constructed using PDF conversion. Ethoxyethylene malonitrile was synthesized from malonitrile by the mature method, and then reacted with alkylhydrazine hydrochloride to produce the corresponding pyrazole o ‐aminonitrile.…”

Section: Resultsmentioning

confidence: 99%

“…Based on our previous studies, [17] pyrazolopyrimidinone skeleton 1 was rapidly constructed using PDF conversion. Ethoxyethylene malonitrile…”

Section: Chemistrymentioning

confidence: 99%

“…[ 13–16 ] To develop the practical value of this transformation, and considering that pyrazolo[3,4‐ d ]pyrimidin‐4‐one is an isomer of the sildenafil core skeleton, pyrazolo[4,3‐ d ]pyrimidin‐7‐one, we have also constructed a series of pyrazolo[3,4‐ d ]pyrimidin‐4‐one skeleton compounds via PDF conversion of 5‐aminopyrazole nitrile with aromatic aldehydes. [ 17 ] Therefore, we designed a series of novel compounds based on the principle of the electronic isometric body (Figure 2). Herein, we will report the design and synthesis of novel isosteric electrons of sildenafil and their anti‐PDE‐5 activities in detail.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and properties of sildenafil isostere

Zhang

Zhao

et al. 2021

Archiv der Pharmazie

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A series of novel pyrazolo[3,4‐d]pyrimidin‐4‐one derivatives were synthesized and evaluated for their anti‐phosphodiesterase‐5 (PDE‐5) activity. A total of 28 compounds, containing alkyl and aryl groups at the 1‐N and 3‐C positions on the pyrazole ring, and also bearing different alkyl substituents on the piperazine ring were synthesized. Four compounds (4d, 5d, 6d, and 5o) were found to have better inhibitory activity against PDE‐5 (IC50 < 10 nM). All four of the most active compounds contain a phenyl ring at the N1 position. Compounds containing a 3,5‐dimethylpiperazinyl group show better activity than others. These results suggest that compound 5o can be used as a lead structure for developing new inhibitors of PDE‐5.

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Section: Resultsmentioning

confidence: 99%

“…Based on our previous studies, [17] pyrazolopyrimidinone skeleton 1 was rapidly constructed using PDF conversion. Ethoxyethylene malonitrile…”

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and properties of sildenafil isostere

Zhang

Zhao

et al. 2021

Archiv der Pharmazie

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“…In this context, tandem reactions which allow multiple chemical transformations in one pot have been recognized as a rather valuable strategy in realizing organic synthesis with high efficiency . Because of these significant advantages, tandem reactions have been a popular strategy for the rapid synthesis of small molecules, especially in the synthesis of drug like structures and natural products …”

Section: Introductionmentioning

confidence: 99%

One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides

et al. 2018

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A novel one-pot tandem process involving Knoevenagel condensation, Michael addition, selective amidation, and Paal–Knorr cyclization to diverse functionalized 3-hydroxy-2-furanyl-acrylamides from simple 2-oxoaldehydes and aroylacetonitriles was presented. Attempts were also made to expand the scope of the reaction to different 2-heteroarylfurans. The packing diagram of the molecules viewed down along the α-axis of the unit cell showed a characteristic intramolecular classical O–H···O hydrogen bond between hydroxyl and carbonyl O atoms leading to self-associated ( Z )-2-furanyl-acrylamides.

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Metal‐ and Catalyst‐Free Electrochemical Synthesis of Quinazolinones from Alkenes and 2‐Aminobenzamides

et al. 2019

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A metal‐ and catalyst‐free electrochemical approach to the preparation of quinazolinones with alkenes and 2‐aminobenzamides via selective anodic oxidative difunctionalization/C−C bond cleavage/cyclization/oxidation has been developed. The synthesis process features convenient operation, low cost, and environmental friendliness, which make it a promising method for the preparation of quinazolinone derivatives.

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Base-catalyzed one-pot tandem reaction: an effective strategy for the synthesis of pyrazolo[3,4-d]pyrimidinone derivatives

Cited by 10 publications

References 34 publications

Synthesis and properties of sildenafil isostere

Synthesis and properties of sildenafil isostere

One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides

Metal‐ and Catalyst‐Free Electrochemical Synthesis of Quinazolinones from Alkenes and 2‐Aminobenzamides

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