Publication
Title
A new synthesis of benzo[f]isoindole-4,9-diones by radical alkylation and bromomethylation of 1,4-naphthoquinones
Author
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-alpha-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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Language
English
Source (journal)
European journal of organic chemistry. - Weinheim, 1998, currens
Publication
Weinheim : 2009
ISSN
1434-193X [print]
1099-0690 [online]
DOI
10.1002/EJOC.200900562
Volume/pages
28 (2009) , p. 4882-4892
ISI
000270500300018
Full text (Publisher's DOI)
Full text (publisher's version - intranet only)
UAntwerpen
Faculty/Department
Publication type
Subject
External links
Web of Science
Record
Identifier
Creation 28.01.2013
Last edited 07.02.2023
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