Rh(III)-Catalyzed Synthesis of Amino-isocoumarins with N-Functionalized Cyclic Carbonates via C-H/O-H Annulation

Org Lett. 2022 Dec 23;24(50):9222-9227. doi: 10.1021/acs.orglett.2c03739. Epub 2022 Dec 13.

Abstract

A practical method to access amino-isocoumarins catalyzed by a Rh(III) complex through redox-neutral C-H/O-H annulation has been disclosed. The use of N-functionalized cyclic carbonates is crucial to facilitate the catalytic turnover, and a broad spectrum of amino-isocoumarin derivatives were prepared with satisfactory yields. Amino-isocoumarin estrone conjugated with a selenocyano functionality was identified to be nearly four times as active as the marketed drug abiraterone against T47D cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonates*
  • Catalysis
  • Isocoumarins*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Isocoumarins
  • Carbonates