Details
| Original language | English |
|---|---|
| Pages (from-to) | 6943-6945 |
| Number of pages | 3 |
| Journal | Journal of Organic Chemistry |
| Volume | 73 |
| Issue number | 17 |
| Publication status | Published - 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.
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Journal of Organic Chemistry, Vol. 73, No. 17, 05.08.2008, p. 6943-6945.
Research output: Contribution to journal › Article › Research › 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 -