Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones
Özet
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.
Sürdürülebilir Kalkınma Amaçları
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SKA 3: Sağlıklı Bireyler
Atıf için künye
Erden, I., Özer, G., Hoarau, C., Cao, W., Song, J., Gaertner, C., Baumgardt, I., & Butenschoen, H. (2008). Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones. JOURNAL OF ORGANIC CHEMISTRY, 73(17), 6943–6945. https://doi.org/10.1021/jo801192z
BibTeX
@article{erden2008-334676,
author = {Erden, Ihsan and Özer, Galip and Hoarau, Christophe and Cao, Weiguo and Song, Jiangao and Gaertner, Christian and Baumgardt, Ingmar and Butenschoen, Holger},
title = {Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones},
journal = {JOURNAL OF ORGANIC CHEMISTRY},
year = {2008},
volume = {73},
number = {17},
pages = {6943--6945},
issn = {0022-3263},
doi = {10.1021/jo801192z},
url = {https://akademik.atauni.edu.tr/yayinlar/334676-photooxygenation-of-5-dialkylamino-4-pyrrolin-3-ones-synthesis-of-highly}
}