A new synthesis of benzo[f]isoindole-4,9-diones by radical alkylation and bromomethylation of 1,4-naphthoquinones

Deblander, Jurgen; Van Aeken, Sam; Jacobs, Jan; De Kimpe, Norbert; Abbaspour Tehrani, Kourosch

doi:10.1002/EJOC.200900562

Title

A new synthesis of benzo[f]isoindole-4,9-diones by radical alkylation and bromomethylation of 1,4-naphthoquinones

Author

Deblander, Jurgen

Van Aeken, Sam

Jacobs, Jan

De Kimpe, Norbert

Abbaspour Tehrani, Kourosch

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