Synthesis of 3-trimethylsiloxy-1-(furan-3-yl)butadiene and its reactions with dienophiles
| Autor: | M. E. Mironov, Elvira E. Shults, Irina Yu. Bagryanskaya |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Double bond Diene 010405 organic chemistry Chemistry Organic Chemistry Imine 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Furan Organic chemistry Lewis acids and bases Methylene Ene reaction Diels–Alder reaction |
| Zdroj: | Chemistry of Heterocyclic Compounds. 52:364-373 |
| ISSN: | 1573-8353 0009-3122 |
| DOI: | 10.1007/s10593-016-1897-4 |
| Popis: | 3-Trimethylsilyloxy-1-(furan-3-yl)butadiene was synthesized and studied in reactions with 2,2-dimethyl-5-methylidene-1,3-dioxane-4,6-diones, 5-methylenepyrimidine-2,4,6-triones, as well as with imines. Reactions with dienophiles containing an exo-methylene double bond in the presence of L-proline occurred regio- and stereoselectively with the formation of 7-(furan-3-yl)spiro[5,5]undecane-1,5,9-triones or 7-(furan-3-yl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraones. The reaction of diene with methylene imine, obtained from L-phenylalanine methyl ester and formaldehyde, in the presence of Lewis acids led to the formation of 2-(furan-3-yl)piperidin-4-one or the product of ene reaction, methyl (2S)-2-{[(4E)-5-(furan-3-yl)-3-oxopent-4-en-1-yl]amino}-3-phenylpropanoate. The structures of three compounds were confirmed by X-ray structural analysis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|