Convenient Michael Addition/beta-Elimination Approach to the Synthesis of 4-Benzyl- and 4-Aryl-selenyl Coumarins using Diselenides as Selenium Sources

PADILHA, G.; BIRMANN, P.T.; DOMINGUES, M; KAUFMAN, T.S.; SAVEGNANO, L; SILVEIRA, C. C.

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2017 vol. 58 p. 985 - 990

0040-4039

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/â-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.