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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Autores principales: Miao, Xiao-Yu, Hu, Yong-Ji, Liu, Fu-Rao, Sun, Yuan-Yuan, Sun, Die, Wu, An-Xin, Zhu, Yan-Ping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571537/
https://www.ncbi.nlm.nih.gov/pubmed/36234926
http://dx.doi.org/10.3390/molecules27196381
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author Miao, Xiao-Yu
Hu, Yong-Ji
Liu, Fu-Rao
Sun, Yuan-Yuan
Sun, Die
Wu, An-Xin
Zhu, Yan-Ping
author_facet Miao, Xiao-Yu
Hu, Yong-Ji
Liu, Fu-Rao
Sun, Yuan-Yuan
Sun, Die
Wu, An-Xin
Zhu, Yan-Ping
author_sort Miao, Xiao-Yu
collection PubMed
description 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.
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spelling pubmed-95715372022-10-17 Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches Miao, Xiao-Yu Hu, Yong-Ji Liu, Fu-Rao Sun, Yuan-Yuan Sun, Die Wu, An-Xin Zhu, Yan-Ping Molecules Article 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. MDPI 2022-09-27 /pmc/articles/PMC9571537/ /pubmed/36234926 http://dx.doi.org/10.3390/molecules27196381 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Miao, Xiao-Yu
Hu, Yong-Ji
Liu, Fu-Rao
Sun, Yuan-Yuan
Sun, Die
Wu, An-Xin
Zhu, Yan-Ping
Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches
title Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches
title_full Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches
title_fullStr Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches
title_full_unstemmed Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches
title_short Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches
title_sort synthesis of diversified pyrazolo[3,4-b]pyridine frameworks from 5-aminopyrazoles and alkynyl aldehydes via switchable c≡c bond activation approaches
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571537/
https://www.ncbi.nlm.nih.gov/pubmed/36234926
http://dx.doi.org/10.3390/molecules27196381
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