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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Development of a diversity-oriented approach to oxazole-5-amide libraries
Mark J Thompson1, Harry Adams, Beining Chen
1Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK.
Abstract:
A highly versatile route to oxazole-5-amides is presented. Conversion of readily accessible oxazole-5-trifluoroacetamides into their Boc-protected 5-aminooxazole derivatives provides intermediates amenable to parallel amide synthesis utilizing a reliable, one-pot, acylation-deprotection procedure. During preparation of the N-Boc compounds from trifluoroacetamides, a competing intramolecular rearrangement giving rise to novel N-(oxazol-5-yl)-2,2,2-trifluoroacetimidates was identified, the extent of which is primarily determined by the choice of reaction conditions.
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