4,5-Dihydro-1,2,4-oxadiazole as a Single Nitrogen Transfer Reagent: Synthesis of Functionalized Isoxazoles Assisted by Sc(OTf)3 or Au(I)/Sc(OTf)3 Synergistic Catalysis

Ali Wang; Peizhuo Lv; Yuanhong Liu

doi:10.1021/acs.orglett.3c01566

4,5-Dihydro-1,2,4-oxadiazole as a Single Nitrogen Transfer Reagent: Synthesis of Functionalized Isoxazoles Assisted by Sc(OTf)₃ or Au(I)/Sc(OTf)₃ Synergistic Catalysis

Org Lett. 2023 Jun 16;25(23):4377-4382. doi: 10.1021/acs.orglett.3c01566. Epub 2023 Jun 5.

Authors

Ali Wang¹, Peizhuo Lv¹, Yuanhong Liu¹

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China.

PMID: 37272751
DOI: 10.1021/acs.orglett.3c01566

Abstract

A five-membered N-O heterocycle, 4,5-dihydro-1,2,4-oxadiazole, was found to act as a single nitrogen atom transfer reagent via elimination of a ketone/aldehyde and a nitrile. This reagent was successfully applied for the synthesis of isoxazoles from ynones promoted by Sc(OTf)₃ or through Au(I)/Sc(OTf)₃ synergistic catalysis. The efficiency of this protocol was also demonstrated by its application in modifications of structurally complex natural products and pharmaceuticals.

MeSH terms

Catalysis
Isoxazoles*
Nitrogen
Oxadiazoles
Scandium*

Substances

Scandium
Isoxazoles
Nitrogen
Oxadiazoles