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Revista de la Sociedad Química de México

Print version ISSN 0583-7693


MANJARREZ, Norberto et al. Síntesis de 3-amino-1,2-oxazoles y 3-amino-4,5-dihidro-1,2-oxazoles a partir de nitrilos α,β-insaturados y cetooximas. Rev. Soc. Quím. Méx [online]. 2000, vol.44, n.3, pp.188-193. ISSN 0583-7693.

A general preparation of 3-amino-1,2-oxazoles starting with the addition of ketoximes to α,β-unsaturated nitriles, was studied. The resulting O-alkyl oximes were isolated and characterized; furthermore, the transformation to the corresponding 3-amino-4,5-dihydro-1,2-oxazoles was successfully attained in yields ranging from 45 to 78%. The dehydrogenation leading to the 3-amino-1,2-oxazoles showed the following limitations: the ring must have an aryl or alkyl substituent in the 5 position, and the amino group needs to be protected. γ-MnO2 gave the desired aromatization reaction in 79-87% yield.

Keywords : synthesis; 3-amino-1; 2-oxazoles; aromatization; 3-amino-4; 5-dihydro-1; 2-oxazoles.

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