1448595-30-9Relevant academic research and scientific papers
A Rapid Entry to Diverse γ-Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ-Lactones and Metal-Catalyzed Postfunctionalization
Chopin, Nicolas,Yanai, Hikaru,Iikawa, Shinya,Pilet, Guillaume,Bouillon, Jean-Philippe,Médebielle, Maurice
, p. 6259 - 6269 (2015/10/06)
The synthesis of a series of diverse methyl and benzyl γ-ylidenetetronate derivatives was accomplished through the condensation of methyl and benzyl tetronates with (hetero)aryl aldehydes in a new two- or three-step aldolisation/dehydration sequence. The bromination of methyl and benzyl γ-ylidenetetronates occurred under mild conditions to provide the corresponding C-3-brominated γ-unsaturated lactones. Di- and tribrominated γ-lactones were prepared under slightly different conditions. Some brominated materials were employed in representative Stille, Suzuki-Miyaura, and Sonogashira cross-coupling reactions to yield functionalized methyl and benzyl γ-ylidenetetronate derivatives. Compounds that resulted from the Sonogashira cross-coupling reactions were desilylated and converted into 1,2,3-triazole derivatives through a copper(I)-catalyzed 1,3-dipolar cycloaddition reaction with benzyl azide.
Regioselective bromination of tetronic acid-derived γ-lactones and metal-catalyzed post-functionalization: An efficient access to new γ-ylidenetetronate derivatives
Iikawa, Shinya,Chopin, Nicolas,Pilet, Guillaume,Bouillon, Jean-Philippe,Médebielle, Maurice
, p. 4577 - 4581 (2013/08/23)
The synthesis of several methyl and benzyl γ-ylidenetetronates was accomplished and the bromination reactions of these derivatives, using bromine or N-bromosuccinimide (NBS), were found to occur under mild conditions. Several new brominated γ-unsaturated
