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Synthesis 2018; 50(09): 1875-1882
DOI: 10.1055/s-0037-1609318
DOI: 10.1055/s-0037-1609318
paper
PIFA-Mediated Oxidative Cyclization Reactions of α-Acyl Acrylamides: A Synthetic Route to Substituted Isoxazol-3(2H)-ones
Financial support of this research by the National Natural Science Foundation of China (21502185 and 21542006) is greatly acknowledged.
Weitere Informationen
Publikationsverlauf
Received: 04. Dezember 2017
Accepted after revision: 16. Januar 2018
Publikationsdatum:
21. Februar 2018 (online)
Abstract
An intramolecular cyclization of various α-acyl β-amino acrylamides in the presence of PIFA and TFA is described. This transformation features mild reaction conditions, simple execution, high chemoselectivity, and metal catalyst-free oxidation, and thereby, provides not only an alternative protocol for the construction of N–O bond, but also an efficient and straightforward synthesis of substituted isoxazol-3(2H)-ones from readily available α-acyl acrylamides.
Key words
acrylamides - cyclization - heterocycles - hypervalent iodine reagents - N–O bond formation - isoxazol-3(2H)-onesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609318.
- Supporting Information
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For the aryl hydroxylation mediated by hypervalent iodine reagents, see ref 11b and:
For the aryl hydroxylation catalyzed by transition metals, see: