Title
A new synthesis of benzo[f]isoindole-4,9-diones by radical alkylation and bromomethylation of 1,4-naphthoquinones A new synthesis of benzo[f]isoindole-4,9-diones by radical alkylation and bromomethylation of 1,4-naphthoquinones
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Weinheim ,
Subject
Chemistry
Source (journal)
European journal of organic chemistry. - Weinheim
Volume/pages
(2009) :28 , p. 4882-4892
ISSN
1434-193X
ISI
000270500300018
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
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)
E-info
https://repository.uantwerpen.be/docman/iruaauth/b7026d/7bc2843.pdf
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000270500300018&DestLinkType=RelatedRecords&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000270500300018&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000270500300018&DestLinkType=CitingArticles&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848