One-Pot Synthesis of 1-Hydroxyacridones from para-Quinols and ortho-Methoxycarbonylaryl Isocyanates

J Org Chem. 2020 Mar 20;85(6):4515-4524. doi: 10.1021/acs.joc.9b03307. Epub 2020 Feb 27.

Abstract

A variety of substituted acridones were synthesized via a one-pot, metal-free cascade reaction. In this event, the DBU-mediated addition between quinols and ortho-methoxycarbonylaryl isocyanates formed a bicyclic oxazolidinone, followed by a sequence of intramolecular condensation, tautomerization, and decarboxylation, which led to the formation of acridones. The acridones showed mild activity against the human cytomegalovirus.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Decarboxylation
  • Humans
  • Hydroquinones*
  • Isocyanates*

Substances

  • Hydroquinones
  • Isocyanates