Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches

Miao, Xiaoyu; Hu, Yong-Ji; Liu, Fu-Rao; Sun, Yuanyuan; Sun, Die; Wu, Anxin; Zhu, Yan‐Ping

doi:10.3390/molecules27196381

Cited by 8 publications

(1 citation statement)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis of pyridine derivatives from alkynyl aldehydes 1a and 5-aminopyrazoles 26a was reported by Zhu et al in 2022 ( Scheme 34 ). 46 In this method, Ag, I 2 and NBS were used to activate the C C bond of alkynyl aldehydes 1a. A wide variety of halogen and non-halogen-functionalized pyrazolo[3,4- b ]pyridine compounds 26b, 26c, and 26d were achieved in moderate to good chemical yields.…”

Section: Synthesis Of N-heterocyclic Compoundsmentioning

confidence: 99%

Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes

et al. 2023

View full text Add to dashboard Cite

show abstract

Section: Synthesis Of N-heterocyclic Compoundsmentioning

confidence: 99%

Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes

et al. 2023

View full text Add to dashboard Cite

show abstract

Tailor‐Made Pyrazolopyridines and Fused Pyrazolopyridines: Recent Updates toward Sustainable Synthesis

Alam Mondal,

Ghosh

2024

ChemistrySelect

View full text Add to dashboard Cite

Over the last three decades, owing to labour cost, time and especially environmental issues, one‐pot synthesis of heterocyclic compounds involving tandem or multicomponent (sequential or consecutive) reactions has gained particular attention worldwide. Most of the marketed drug molecules hold one or more heterocyclic rings. Due to some side effects of several drugs along with the gradual emergence of antimicrobial resistance, the necessity for developing new heterocyclic molecules continues; special attention should be paid in this respect towards employing more one‐pot reactions for their syntheses. Pyrazolopyridines are fused heterocycles holding pyridine and pyrazole and possess a wide variety of biological and pharmaceutical properties. Several existing drug molecules also bear pyrazolopyridine scaffolds. The present perspective is an endeavour to encompass green syntheses of different isomeric pyrazolopyridine systems, most of these published during the past five years or more for a few cases.

show abstract

Innovative Ultrasound‐Assisted Synthesis of Isoxazolo[5,4‐b]Pyridines from Aryl Glyoxal, 5‐Aminoisoxazoles, and Malononitrile in Acetic Acid as a Solvent and Catalyst

Alizadeh,

Hosseini

2024

ChemistrySelect

View full text Add to dashboard Cite

In this work, a novel strategy for the straightforward synthesis of isoxazolo[5,4‐b]pyridines from a one‐pot reaction of aryl glyoxal, 5‐aminoisoxazoles, and malononitrile under ultrasound (US) irradiation is described. In the reaction, acetic acid has a dual role as solvent and catalyst. The advantages of this reaction include easy purification of products, raw materials with easy access, short reaction time, high efficiency, and green conditions by utilizing ultrasound irradiation as an energy source and using acetic acid as solvent and Lewis acid. The synthesis achieved high yields of isoxazolo[5,4‐b]pyridines with a broad substrate scope, successfully producing twelve diverse derivatives. The methodology capitalizes on the benefits of sonochemistry, which accelerates reaction rates and improves selectivity while minimizing waste. The proposed mechanism involves a series of reactions including Knoevenagel condensation, Michael addition, and subsequent cyclization processes. This approach not only streamlines the synthesis of complex heterocycles but also aligns with environmentally friendly practices.

show abstract

Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches

Cited by 8 publications

References 57 publications

Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes

Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes

Tailor‐Made Pyrazolopyridines and Fused Pyrazolopyridines: Recent Updates toward Sustainable Synthesis

Innovative Ultrasound‐Assisted Synthesis of Isoxazolo[5,4‐b]Pyridines from Aryl Glyoxal, 5‐Aminoisoxazoles, and Malononitrile in Acetic Acid as a Solvent and Catalyst

Contact Info

Product

Resources

About