Issue 66, 2018

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
08 Jun 2018
Accepted
24 Jul 2018
First published
26 Jul 2018

Chem. Commun., 2018,54, 9178-9181

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

H. Zhao, J. Du, J. Guo, N. Feng, L. Wang, W. Ding and X. Song, Chem. Commun., 2018, 54, 9178 DOI: 10.1039/C8CC04584D

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