A Two-Stage Iterative Process for the Synthesis of Poly-oxazoles

Methodology has been developed to prepare bis-oxazoles via a two-stage iterative process. The sequence begins with C2-chlorination of a lithiated oxazole using hexachloroethane. Generation of the C2−C4 ‘ bond by SNAr substitution with TosMIC anion, followed by conversion to the heterocycle in a one-...

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Bibliographic Details
Published inOrganic letters Vol. 7; no. 15; pp. 3351 - 3354
Main Authors Atkins, Jeffery M, Vedejs, Edwin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.07.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Molecular Structure
Oxazoles - chemical synthesis
Oxazoles - chemistry
Physical Sciences
Polymers - chemical synthesis
Polymers - chemistry
Science & Technology
SUBSTITUTED OXAZOLES
ORGANIC-SYNTHESIS
TELOMERASE INHIBITOR
REAGENTS
DIAZONAMIDE-A
BIS-OXAZOLE
HALOGEN EXCHANGE
TELOMESTATIN
DERIVATIVES
ALPHA-METALATED ISOCYANIDES
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Summary:Methodology has been developed to prepare bis-oxazoles via a two-stage iterative process. The sequence begins with C2-chlorination of a lithiated oxazole using hexachloroethane. Generation of the C2−C4 ‘ bond by SNAr 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.
Bibliography:Medline
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol051244x