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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A two-stage iterative process for the synthesis of poly-oxazoles
Jeffery M Atkins1, Edwin Vedejs
1Department of Chemistry, University of Michigan, Ann Arbor, 48109, USA.
Abstract:
[reaction: see text]. Methodology has been developed to prepare bis-oxazoles via a two-stage iterative process. The sequence begins with C(2)-chlorination of a lithiated oxazole using hexachloroethane. Generation of the C(2)-C(4)(') bond by S(N)Ar substitution with TosMIC anion, followed by conversion to the heterocycle in a one-pot reaction with glyoxylic acid monohydrate, affords the desired bis-oxazole in good yield and purity. The two-stage process allows for efficient synthesis of a tris-oxazole and the first iterative preparation of a tetra-oxazole.
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