877-39-4Relevant articles and documents
A practical approach to the synthesis of 2,4-disubstituted oxazoles from amino acids
Morwick, Tina,Hrapchak, Matt,DeTuri, Molly,Campbell, Scot
, p. 2665 - 2668 (2007/10/03)
(Matrix presented) A new sequence for the synthesis of various 2,4-disubstituted oxazoles from α-amino acids is reported. The method is shown to be general and incorporates the reagent combination, triphenylphosphine/hexachloroethane, for cyclodehydration of intermediate α-acylamino aldehydes. Implementation of this reagent system for the conversion of α-acylamino ketones to oxazoles is briefly investigated.
Chemistry of 5-oxodihydroisoxazoles. Part 18. Synthesis of oxazoles by the photolysis and pyrolysis of 2-acyl-5-oxo-2,5-dihydroisoxazoles
Prager, Rolf H.,Smith, Jason A.,Weber, Ben,Williams, Craig M.
, p. 2665 - 2672 (2007/10/03)
N-Acylisoxazol-5-ones lose carbon dioxide under photochemical and thermal conditions affording iminocarbenes which undergo intramolecular cyclisation through the oxygen of the acyl group to give oxazoles. Under photochemical conditions those acylisoxazolones with electron withdrawing groups at C-4 usually give high yields of oxazoles, while those with electron donating groups at C-4 give only poor yields: the reverse is observed under thermal conditions.
SYNTHESE DE PYRROLES ET D'OXAZOLES PAR PYROLYSE DE N-(HYDROXY-2' ETHYL) AMINO-3 PROPENOATE
Pale-Grosdemange, Catherine,Chuche, Josselin
, p. 3397 - 3414 (2007/10/02)
The gas phas pyrolysis of various N-(2'-hydroxyethyl)-3-amino propenoates 1-6 and N-(2'-hydroxy-2'-phenyl ethyl)-3-amino propanoate 7-9 at 390 deg C-420 deg C leads respectively to formylpyrroles 11-16 and benzoylpyrroles 17-19 and, in some cases, to substituted oxazoles 36-39.The results are best explained by the intermediate formation of a dicarbonyl derivative followed either by an intramolecular thermal crotonisation or a six ? electrocyclization of an azomethine ylide.