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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Published in | Organic letters Vol. 7; no. 15; pp. 3351 - 3354 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
21.07.2005
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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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. |
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Bibliography: | Medline NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol051244x |