Dissertação
Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
Fecha
2019-02-19Autor
Dilelio, Marina Cardoso
Institución
Resumen
In this work we developed a methodology for the synthesis of 1,3-oxazines
derived from aminocoumarins by the hydroxymethylation/acetalization reaction with
aldehydes catalyzed by H2SO4 in aqueous media. The scope and limitations of this
methodology were also studied, presenting good results for different substrates.
Twelve compounds were obtained with 34 to 90% yields.
Subsequently, N-propargylation of one of the 1,3-oxazines was performed, and
then the 1,3-dipolar cycloaddition was carried out with different organic azides,
obtaining five 1,4-dissubstituted 1,2,3-triazoles, with 65 to 96% yields.
Some selected coumpounds presented antifungal activity against Candida
krusei, Candida dublieneses, Candida glabrata and Candida tropicalis. The
photophysical properties of the compounds were analyzed, presenting high quantum
yields of fluorescence (up to Φf = 0.69) and large Stokes shifts (up to 201 nm).