Rh(III)-Catalyzed Oxidative Annulation of Isoquinolones with Diazoketoesters Featuring an in Situ Deacylation: Synthesis of Isoindoloisoquinolones and Their Transformation to Rosettacin Analogues

The Journal of Organic Chemistry
Shenghai GuoXuesen Fan

Abstract

A novel and practical procedure for the preparation of isoindolo[2,1- b]isoquinoline-7-carboxylate derivatives through a Rh(III)-catalyzed oxidative [4 + 1] cycloaddition of isoquinolones with diazoketoesters followed by an in situ deacylation reaction is disclosed. Intriguingly, the title compounds could be easily converted into isoindolo[2,1- b]isoquinolin-5(7 H)-ones via de-esterification, which are rosettacin analogues and frequently found in various natural alkaloids and synthetic drug molecules.

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Citations

Feb 1, 2019·Organic & Biomolecular Chemistry·Kangkan TalukdarTharmalingam Punniyamurthy
Apr 11, 2019·Organic & Biomolecular Chemistry·Hitesh Kumar SainiAnil Kumar
May 20, 2020·Chemistry : a European Journal·Herbert WaldmannCarsten Strohmann
Sep 8, 2021·Chemistry : a European Journal·Genesis Infante, Sara Eisler

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