info:eu-repo/semantics/article
Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
Registro en:
Padilha, Gustavo; Birmann, Paloma T.; Domingues, Micaela; Kaufman, Teodoro Saul; Savegnano, Lucielli; et al.; Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 58; 10; 3-2017; 985-990
0040-4039
CONICET Digital
CONICET
Autor
Padilha, Gustavo
Birmann, Paloma T.
Domingues, Micaela
Kaufman, Teodoro Saul
Savegnano, Lucielli
Silveira, Claudio
Resumen
A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus. Fil: Padilha, Gustavo. Universidade Federal de Santa Maria; Brasil Fil: Birmann, Paloma T.. Universidade Federal de Pelotas; Brasil Fil: Domingues, Micaela. Universidade Federal de Pelotas; Brasil Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Savegnano, Lucielli. Universidade Federal de Pelotas; Brasil Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil