Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 21, Pages 10777-10786Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01977
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Funding
- National Natural Science Foundation of China [21372068]
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Carbonyl-containing oxindoles can be prepared from N-arylacrylamides and alpha-diketones by TBHP- or oxone (KHSO5)-mediated C(sp(2))-C(sp(2)) bond cleavage and new C(sp(2))-C(sp(3)) bond formation. This methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing inexpensive and readily available reagents, thus providing a practical and efficient approach to an important class of 3-(2-oxoethyl)indolin-2-ones which are highly valued synthetic intermediates of biologically active molecules. In this transformation, alkylcarbonyl-containing oxindoles were obtained in majority when N-arylacrylamides reacted with asymmetric aliphatic/aromatic alpha-diketones. On the basis of the preliminary experiments, a plausible mechanism of this transformation is disclosed.
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