Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 6943-6945 |
| Seitenumfang | 3 |
| Fachzeitschrift | Journal of Organic Chemistry |
| Jahrgang | 73 |
| Ausgabenummer | 17 |
| Publikationsstatus | Veröffentlicht - 5 Aug. 2008 |
Abstract
(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.
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- Organische Chemie
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in: Journal of Organic Chemistry, Jahrgang 73, Nr. 17, 05.08.2008, S. 6943-6945.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. Synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones
AU - Erden, Ihsan
AU - Özer, Galip
AU - Hoarau, Christophe
AU - Cao, Weiguo
AU - Song, Jiangao
AU - Gärtner, Christian
AU - Baumgardt, Ingmar
AU - Butenschön, Holger
PY - 2008/8/5
Y1 - 2008/8/5
N2 - (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.
AB - (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.
UR - http://www.scopus.com/inward/record.url?scp=51549088781&partnerID=8YFLogxK
U2 - 10.1021/jo801192z
DO - 10.1021/jo801192z
M3 - Article
C2 - 18680344
AN - SCOPUS:51549088781
VL - 73
SP - 6943
EP - 6945
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 17
ER -