Molecules (Feb 2024)

Dearomatization of 3-Aminophenols for Synthesis of Spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones via Hydride Transfer Strategy-Enabled [5+1] Annulations

  • Jia-Cheng Ge,
  • Yufeng Wang,
  • Feng-Wei Guo,
  • Xiangyun Kong,
  • Fangzhi Hu,
  • Shuai-Shuai Li

DOI
https://doi.org/10.3390/molecules29051012
Journal volume & issue
Vol. 29, no. 5
p. 1012

Abstract

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The Sc(OTf)3-catalyzed dearomative [5+1] annulations between readily available 3-aminophenols and O-alkyl ortho-oxybenzaldehydes were developed for synthesis of spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones. The “two-birds-with-one-stone” strategy was disclosed by the dearomatization of phenols and direct α-C(sp3)–H bond functionalization of oxygen through cascade condensation/[1,5]-hydride transfer/dearomative-cyclization process. In addition, the antifungal activity assay and derivatizations of products were conducted to further enrich the utility of the structure.

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