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Isoxazole to oxazole: a mild and unexpected transformation

Year: 2014

Type: article

Abstract: 3-Aryltetrahydrobenzisoxazoles prepared en route to the coleophomone natural products and analogues, were found to undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this unprecedented, facile transformation was probed: a range of analogues was produced, a mechanism proposed, and an application demonstrated by synthesis of a known herbicidal compound.

Source: Chemical Communications

DOI: 10.1039/c4cc07999j

Authors: Raymond C. F. Jones, Alexander Chatterley, Romain Marty, W. Martin Owton, Mark R. J. Elsegood

Institutions: Loughborough University, Eli Lilly (United Kingdom)

Language: English

Topic: Chemical synthesis and pharmacological studies

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

OpenAlex ID: W2040160332

FWCI: 2.198

Cites: 21

Cited by: 42

Related to: 10