1049037-82-2Relevant academic research and scientific papers
Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. Synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones
Erden, Ihsan,Oezer, Galip,Hoarau, Christophe,Cao, Weiguo,Song, Jiangao,Gaertner, Christian,Baumgardt, Ingmar,Butenschoen, Holger
, p. 6943 - 6945 (2008/12/22)
(Chemical Equation Presented) 5-Dialkylamino-4-pyrrolin-3-ones, available from cyclocondensation of amidines with dimethyl acetylenedicarboxylate (DMAD), undergo rapid singlet oxygenation to give highly functionalized ureas by way of a 1,2-dioxetane cleavage of the initially formed [2 + 2] cycloadducts. These latter compounds undergo cyclization to 2-oxazolidinones in MeOH. Catalytic hydrogenation of the ureas in EtOAc gives 2-oxazolinones. The DBU-DMAD adduct undergoes photooxygenation by an entirely different pathway to give a large ring heterocycle.
