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Synthesis of Isoxazoles via One-Pot Oxidation/Cyclization Sequence from Propargylamines

Mengyan Duan, Guodong Hou, Yabiao Zhao, Congjun Zhu, Chuanjun Song

2022The Journal of Organic Chemistry24 citationsDOI

Abstract

A facile strategy for the synthesis of isoxazoles has been efficaciously developed, which involves oxidation of propargylamines to the corresponding oximes followed by CuCl-mediated intramolecular cyclization of the latter. This protocol shows a straightforward way to construct a series of isoxazole cores with a wide range of functional group compatibility. Meanwhile, a gram-scale experiment and synthetic applications can be successfully operated.

Topics & Concepts

ChemistryIsoxazoleIntramolecular forceCombinatorial chemistryCompatibility (geochemistry)Sequence (biology)StereochemistryChemical engineeringBiochemistryEngineeringCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsClick Chemistry and Applications
Synthesis of Isoxazoles via One-Pot Oxidation/Cyclization Sequence from Propargylamines | Litcius