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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Rhodium- and Non-Metal-Catalyzed Approaches for the Conversion of Isoxazol-5-ones to 2,3-Dihydro-6H-1,3-oxazin-6-ones

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Author(s):
Jurberg, Igor D. [1, 2] ; Davies, Huw M. L. [1]
Total Authors: 2
Affiliation:
[1] Emory Univ, Dept Chem, 1515 Dickey Dr, Atlanta, GA 30322 - USA
[2] Univ Estadual Campinas, Inst Chem, Rua Monteiro Lobato 270, Campinas, SP 13083970 - Brazil
Total Affiliations: 2
Document type: Journal article
Source: ORGANIC LETTERS; v. 19, n. 19, p. 5158-5161, OCT 6 2017.
Web of Science Citations: 13
Abstract

Two approaches were developed for the conversion of isoxazol-5-ones to 2,3-dihydro-6H-1,3-oxazin-6-ones. The first involves dirhodium-catalyzed reaction of aryl diazoacetates, leading to rhodium carbene intermediates that undergo insertion into the N-O bond of isoxazol-5-ones. The second approach involves conversion of the aryldiazoacetates to the corresponding tosylates, followed by reaction with the isoxazol-5-one in a metal-free one-pot procedure. These studies illustrate an alternative method to achieve a carbene-like transformation without requiring a metal catalyst. (AU)

FAPESP's process: 15/20809-4 - Exploring the Chemistry of Isoxazol-5-ones as Versatile Building Blocks in Organic Synthesis
Grantee:Igor Dias Jurberg
Support Opportunities: Regular Research Grants