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A New Synthesis of Benzo[f]isoindole-4,9-diones by Radical Alkylation and Bromomethylation of 1,4-Naphthoquinones

✍ Scribed by Jurgen Deblander; Sam Van Aeken; Jan Jacobs; Norbert De Kimpe; Kourosch Abbaspour Tehrani

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
311 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Two synthetic routes towards substituted benzo[f]isoindole‐4,9‐diones have been developed. One strategy relies on the synthesis of N‐trifluoroacetyl‐protected 2‐(1‐aminoalkyl)‐1,4‐naphthoquinones starting from 1,4‐naphthoquinone and N‐trifluoroacetyl‐α‐amino acids by a Kochi–Anderson oxidative decarboxylation method. Furthermore, it was demonstrated that 2‐(1‐aminoalkyl)‐1,4‐naphthoquinones are suitable precursors for the synthesis of 1‐alkylbenzo[f]isoindole‐4,9‐diones by bromomethylation and subsequent N‐deprotection. Further functionalization by N‐alkylation and bromination resulted in completely and asymmetrically substituted benzo[f]isoindole‐4,9‐diones. The second synthesis is based on a reductive amination of 3‐(bromomethyl)‐1,4‐dimethoxynaphthalene‐2‐carbaldehyde and subsequent oxidation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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