Convenient Michael addition/β-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources

• Published in: Tetrahedron letters Vol. 58; no. 10; pp. 985 - 990
• Main Authors: Padilha, Gustavo, Birmann, Paloma T., Domingues, Micaela, Kaufman, Teodoro S., Savegnago, Lucielli, Silveira, Claudio C.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 08.03.2017; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Functionalized coumarins; Heterocyclic derivatives; Physical Sciences; Science & Technology; Selena-Michael addition/β-elimination; Selenocoumarins; Selenofunctionalization; Heterocyclic derivatives; Selenocoumarins; Selenofunctionalization; Selena-Michael addition/β-elimination; Functionalized coumarins; MAIN ABSORPTION; ACID; SOLID-PHASE SYNTHESIS; VINYLIC CHALCOGENIDES; EFFICIENT ROUTE; ARYLATION; CARBON DOUBLE-BONDS; Selena -Michael addition/beta-elimination; DERIVATIVES; NUCLEOPHILIC ATTACKS; CYCLIZATION
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.01.084

[Display omitted] •Efficient Michael addition/β-elimination approach toward 4-organoselanyl coumarins.•Diselenides as suitable selenium sources for a Michael addition/β-elimination process.•Readily accessible selenium-substituted heterocycles with antioxidant properties.•Antioxidant profile of 4-organoselanyl coumarins in mice cortex and hippocampus. 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.