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

A cascade 6-endo-dig cyclization reaction was developed for the switchable synthesis of halogen and non-halogen-functionalized pyrazolo[3,4-b]pyridines from 5-aminopyrazoles and alkynyl aldehydes via C≡C bond activation with silver, iodine, or NBS. In addition to its wide substrate scope, the reacti...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-09, Vol.27 (19), p.6381
Main Authors: Miao, Xiao-Yu, Hu, Yong-Ji, Liu, Fu-Rao, Sun, Yuan-Yuan, Sun, Die, Wu, An-Xin, Zhu, Yan-Ping
Format: Article
Language:English
Subjects:
6-endo-dig cyclization
Aldehydes
alkyne activation
Chemical bonds
Chemical tests and reagents
Chromatography
Functional groups
Iodine
Natural products
NMR
Nuclear magnetic resonance
pyrazolo[3,4-b]pyridine
Pyridine
Pyridines
regional selectivity
Resveratrol
Selectivity
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Summary:A cascade 6-endo-dig cyclization reaction was developed for the switchable synthesis of halogen and non-halogen-functionalized pyrazolo[3,4-b]pyridines from 5-aminopyrazoles and alkynyl aldehydes via C≡C bond activation with silver, iodine, or NBS. In addition to its wide substrate scope, the reaction showed good functional group tolerance as well as excellent regional selectivity. This new protocol manipulated three natural products, and the arylation, alkynylation, alkenylation, and selenization of iodine-functionalized products. These reactions demonstrated the potential applications of this new method.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27196381