DMAP-Catalyzed Reaction of Diethyl 1,3-Acetonedicarboxylate with 2-Hydroxybenzylideneindenediones: Facile Synthesis of Fluorenone-Fused Coumarins

Dedicated to Professor Adrian Schwan of the University of Guelph on the occasion of his 60^th birthday

Abstract

The base-catalyzed reaction of diethyl 1,3-acetonedicarboxylate with 2-hydroxybenzylidene indenediones was studied. The reaction provides a facile and expeditious protocol for the synthesis of natural product inspired fluorenone-fused coumarins in good to very good yields. This process resembles a combination of domino Michael–intramolecular Knoevenagel–aromatization–lactonization reactions in a single step. Although this reaction operates with many bases, the best yields were obtained with DMAP as a catalyst. This protocol could open new potential avenues for the synthesis of fused coumarins by the reaction of substituted β-keto esters with different 2-(2-hydroxybenzylidenes) of 1,3-dicarbonyl compounds.

Key words

coumarin - fluorenone - indandione - DMAP - benzo[c]chromen-6-ones

Publication History

Received: 02 January 2021

Accepted after revision: 07 February 2021

Accepted Manuscript online:
07 February 2021

Article published online:
18 February 2021

• References and Notes

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