Reactivity of Unsaturated 5(4H)-Oxazolones with Hg(II) Acetate: Synthesis of Methyl N-Benzoylamino-3-arylacrylates

Abstract

An efficient and high-yield procedure to prepare methyl N-benzoylamino-3-arylacrylates from unsaturated (Z)-2-aryl-4-arylidene-5-(4H)-oxazolones and Hg(OAc)₂ in methanol is described herein. The observed reactivity of mercury(II) acetate here is different than its usual metallating behavior and it cleaves the unsaturated oxazolone ring without change of stereochemistry.

GRAPHICAL ABSTRACT

Keywords:

• Alcoholysis
• azalactone ring opening
• mercury(II) acetate
• 5-(4H)-oxazolones

ACKNOWLEDGMENTS

Funding from CNCSIS TD87/2007 (Romania), the Ministerio de Ciencia e Innovacion (Projects CTQ2008-01784 and CTQ2007-62245, Spain), and Gobierno de Aragon (PI071-09) is gratefully acknowledged. D. R. also thanks the World Federation of Scientists (WFS) for financial support.

Notes

^a 1 − x, 2 − y, 1 − z.

^b 1 + x, 1 + y, z.

^c 2 + x, 1 + y, z.