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

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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.

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Acknowledgements

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

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Authors and Affiliations

  1. Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, 1475, Budapest, Hungary

    Csilla Hargitai, Györgyi Koványi-Lax, Tamás Nagy, András Dancsó, Judit Halász, Gábor Tóth, Gyula Simig & Balázs Volk

  2. Medicinal Chemistry Research Group, Hungarian Academy of Sciences, Research Centre for Natural Sciences, P.O. Box 286, 1519, Budapest, Hungary

    Péter Ábrányi-Balogh

Authors
  1. Csilla Hargitai
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  2. Györgyi Koványi-Lax
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  3. Tamás Nagy
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  4. Péter Ábrányi-Balogh
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  5. András Dancsó
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  6. Judit Halász
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  7. Gábor Tóth
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  8. Gyula Simig
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  9. Balázs Volk
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Correspondence to Balázs Volk.

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706_2019_2395_MOESM1_ESM.pptx

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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Hargitai, C., Koványi-Lax, G., Nagy, T. et al. Interesting transformations of methylenedioxy-substituted ortho-(pivaloylaminomethyl)benzaldehyde. Monatsh Chem 150, 1121–1125 (2019). https://doi.org/10.1007/s00706-019-02395-6

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  • DOI: https://doi.org/10.1007/s00706-019-02395-6

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