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Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 6, pp 1121–1125 | Cite as

Interesting transformations of methylenedioxy-substituted ortho-(pivaloylaminomethyl)benzaldehyde

  • Csilla Hargitai
  • Györgyi Koványi-Lax
  • Tamás Nagy
  • Péter Ábrányi-Balogh
  • András Dancsó
  • Judit Halász
  • Gábor Tóth
  • Gyula Simig
  • Balázs VolkEmail author
Original Paper
  • 68 Downloads

Abstract

Under acidic conditions, methylenedioxy-substituted ortho-(pivaloylaminomethyl)benzaldehyde underwent a surprising rearrangement reaction leading to the regioisomer of the starting compound as the major product and a dimer-type aldehyde as the minor one. The supposed reaction mechanisms are given below providing a feasible explanation for the formation of both products. Isoindole, proposed as the key intermediate for the formation of the products, was trapped in a Diels–Alder cycloaddition carried out with N-phenylmaleimide.

Graphical abstract

Keywords

Ring-chain tautomerism Isoindoles Reaction mechanism Diels–Alder reaction Rearrangement 

Notes

Acknowledgements

We are grateful to Ms. Ferencné Kertész for technical assistance in the reactions.

Supplementary material

706_2019_2395_MOESM1_ESM.pptx (223 kb)
Supplementary material 1 1H, 13C, HSQC, HMBC spectra and assignment of new compound 5, and 1H, 13C, HSQC, HMBC, COSY, NOESY, ROESY spectra and assignment of new compound 6 (PPTX 224 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Directorate of Drug Substance DevelopmentEgis Pharmaceuticals Plc.BudapestHungary
  2. 2.Medicinal Chemistry Research GroupHungarian Academy of Sciences, Research Centre for Natural SciencesBudapestHungary

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