Direct synthesis of benzoisoindole-1,3-diones and naphtho[1,2-c]furan-1,3-diones via Cu-promoted Diels-Alder reaction of vinyl arenes as dienes and maleimides

Document Type : Original Article

Authors

University of Guilan

Abstract

Fusion of a ring segment through the formation of two new bonds at the expense of two other (weaker) bonds is a transformation which were always at the center of chemists‘ attention. Maleimides have aspiration for involvement of both their olefinic carbons in the reactions in which they take part. In this study, for the first time the synthesis of benzo [e] isoindole-1,3- diones using copper promoted one pot reaction of styrene derivatives with maleimides is reported. This is the first report on the Diels-Alder reaction of styrenes as dienes with the ene systems. in addition, valuable naphtho [1,2-c] furan-1,3- diones derivatives are synthesized via the reaction of maleic anhydrides with styrenes (using maleic anhydride instead of derivatives of maleimide). Use of commercially available styrenes as raw materials as well as the direct synthetic strategy of the invented procedure led to high yields of products for the synthetic organic chemists.

Keywords

References

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Iranian Journal of Chemistry
Volume 3, Issue 1 - Serial Number 4
September 2020
Pages 7-14

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History

  • Receive Date: 12 July 2019
  • Revise Date: 20 October 2019
  • Accept Date: 30 November 2019

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