Enantiospecific electrochemical rearrangement for the synthesis of hindered triazolopyridinone derivatives

Zenghui Ye, Yanqi Wu, Na Chen, Hong Zhang, Kai Zhu, Mingruo Ding, Min Liu, Yong Li and Fengzhi Zhang ()
Additional contact information
Zenghui Ye: Zhejiang University of Technology
Yanqi Wu: Zhejiang University of Technology
Na Chen: Zhejiang University of Technology
Hong Zhang: Zhejiang University of Technology
Kai Zhu: Zhejiang University of Technology
Mingruo Ding: Zhejiang University of Technology
Min Liu: Zhejiang University of Technology
Yong Li: Zhejiang University of Technology
Fengzhi Zhang: Zhejiang University of Technology

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Triazolopyridinone derivatives are of high value in both medicinal and material chemistry. However, the chiral or hindered triazolopyridinone derivatives remain an underexplored area of chemical space because they are difficult to prepare via conventional methods. Here we report an electrochemical rearrangement for the efficient synthesis of otherwise inaccessible triazolopyridinones with diverse alkyl carboxylic acids as starting materials. This enables the efficient preparation of more than 60 functionalized triazolopyridinones under mild conditions in a sustainable manner. This method is evaluated for the late stage modification of bioactive natural products, amino acids and pharmaceuticals, and it is further applied to the decagram scale preparation of enantiopure triazolopyridinones. The control experiments support a mechanism involving an oxidative cyclization and 1,2-carbon migration. This facile and scalable rearrangement demonstrates the power of electrochemical synthesis to access otherwise-inaccessible triazolopyridinones and may find wide application in organic, material and medicinal chemistry.

Date: 2020
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-020-17389-w Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-17389-w

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-020-17389-w

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().