Formal [5+2] cycloaddition of vinylethylene carbonates to oxazol-5-(4H)-ones for the synthesis of 3,4-dihydrooxepin-2(7H)-ones

Formal [5+2] cycloaddition of vinylethylene carbonates to oxazol-5-(4H)-ones for the synthesis of 3,4-dihydrooxepin-2(7H)-ones

Under the catalysis of Pd2(dba)3 (2.5 mol%), PPh3 (10.0 mol%) and TMSCl (1.0 eq.), the formal [5+2] cycloaddition of vinylethylene carbonates to oxazol-5-(4H)-ones proceeded readily in THF at 60 °C to r.t., thus furnishing 3,4-dihydrooxepin-2(7H)-ones in 67-99% chemical yields. The chemical structur...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (66), p.9178-9181
Hauptverfasser: Zhao, Hong-Wu, Du, Juan, Guo, Jia-Ming, Feng, Ning-Ning, Wang, Li-Ru, Ding, Wan-Qiu, Song, Xiu-Qing
Format: Artikel
Sprache:eng
Schlagworte:
Carbonates
Catalysis
Chemical synthesis
Cycloaddition
Organic chemistry
X-ray diffraction
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Zusammenfassung:Under the catalysis of Pd2(dba)3 (2.5 mol%), PPh3 (10.0 mol%) and TMSCl (1.0 eq.), the formal [5+2] cycloaddition of vinylethylene carbonates to oxazol-5-(4H)-ones proceeded readily in THF at 60 °C to r.t., thus furnishing 3,4-dihydrooxepin-2(7H)-ones in 67-99% chemical yields. The chemical structure of one compound was confirmed by X-ray diffraction analysis, and the others were suggested by inference.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc04584d