Molecules (Dec 2022)

A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated <i>Ortho</i>-Quinone Methides with Isocyanides

  • Huaxin Lin,
  • Senling Tang,
  • Yang Pan,
  • Peng Liang,
  • Xiaofeng Ma,
  • Wei Jiao,
  • Huawu Shao

DOI
https://doi.org/10.3390/molecules27238538
Journal volume & issue
Vol. 27, no. 23
p. 8538

Abstract

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A new approach for the synthesis of 2-aminobenzofurans has been described via Sc(OTf)3 mediated formal cycloaddition of isocyanides with the in situ generated ortho-quinone methides (o-QMs) from o-hydroxybenzhydryl alcohol. Notably, as a class of readily available and highly active intermediates, o-QMs were first used in the construction of benzofurans. This [4 + 1] cycloaddition reaction provides a straightforward and efficient methodology for the construction of 2-aminobenzofurans scaffold in good yield (up to 93% yield) under mild conditions.

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