61652-54-8Relevant academic research and scientific papers
An unexpected Pummerer rearrangement in the synthetic route to ethyl (2′-hydroxy-4′,5′-methylenedioxyphenyl)acetate: An alternative approach to 2,3-dimethylthio benzofurans
Carre?o-Montero, Ariel,Maldonado, Luis A.,Chávez, María Isabel,Hernández-Ortega, Simón,Delgado, Guillermo
, (2019/11/03)
The synthesis of ethyl (2′-hydroxy-4′,5′-methylendioxophenyl)acetate, a fragment of the antihyperglycemic natural coumarin subcoriacin, is reported. We found an expeditious route to the title compound in five steps. Final metal catalyzed acid ethanolysis of the vinylic 1,1-methylthio methylsulfoxide derivative afforded the required aryl acetic ester, but in the absence of metal catalyst, an unexpected Pummerer rearrangement produced the 2,3-dimethylthiofuran derivative as the major product. This last result provides an alternative entry to 2,3-dimethlythiobenzofurans.
Alcohol uncaging with fluorescence reporting: Evaluation of o-acetoxyphenyl methyloxazolone precursors
Gagey, Nathalie,Emond, Matthieu,Neveu, Pierre,Benbrahim, Chouaha,Goetz, Bernard,Aujard, Isabelle,Baudin, Jean-Bernard,Jullien, Ludovic
supporting information; experimental part, p. 2341 - 2344 (2009/06/06)
(Chemical Equation Presented) This paper evaluates a series of photolabile protecting groups with built-in fluorescence reporting. They rely on readily available o-acetoxyphenyl methyloxazolones as activated precursors. Alcohol substrates are easily caged. The resulting photoactivable esters exhibit large one- and two-photon uncaging cross sections. The alcohol substrates are quantitatively released in a 1:1 molar ratio with a strongly fluorescent coumarin coproduct that serves as a reporter to quantify substrate delivery.
