Acid-Mediated Highly Regioselective Oxidation of Substituted Furans: A Simple and Direct Entry to Substituted Butenolides

Abstract

The scope and limitations of an expeditious synthesis of substituted butenolides from 3-substituted or 3,4-disubstituted furans is described. The entire process embodies a controlled oxidation of the furan core to a 2,5-dialkoxy-dihydrofuran intermediate and a regioselective acid-catalyzed hydrolysis to the butenolide ­derivative. 3-Substituted furans yield exclusively 2-substituted butenolides. Calculations studies provide substantiation of a proposed mechanism.

Key words

oxidation - furans - substituted butenolides

References

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1

Instituto Canario de Investigación del Cáncer, www.icic.es.

19

Theoretical calculations details are available from the authors upon request.

20

Obtained by integration of the electronic density over the considered atomic basin.