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2(3H)-Oxazolones from α-Hydroxy Amides and Keteneylidenetriphenylphosphorane via a Phoshorus Ylide Cascade (1997)

Löffler, Jonas ; Schobert, Rainer

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 217-220

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ISSN: 0947-3440

Keywords: Phosphorus ylides ; 2(3H)-oxazolones ; Oxazolidines ; Cascade reaction ; N-Heterocycles ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Upon heating in xylene α-hydroxyamides 3 react with the cumulated phosphorus ylide 1 to give the substituted 2(3H)-oxazolones 8 in 40-80% yield. The reaction proceeds via an addition/cyclization/intermolecular-Wittig olefination sequence, which implies three different types of phosphorus ylides of increasing “ylide activity”. Evidence for the proposed mechanism is provided by trapping the intermediate ylide species with suitable carbonyl compounds. This technique may also be used to exclusively prepare the 2,4-oxazolidinediones 13 in good yields.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970132

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