e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Different synthetic routes towards efficient organogelators: 2, 3-substituted anthracenes

JL Pozzo, GM Clavier, M Colomes, H Bouas-Laurent

Index: Pozzo, Jean-Luc; Clavier, Gilles M.; Colomes, Michel; Bouas-Laurent, Henri Tetrahedron, 1997 , vol. 53, # 18 p. 6377 - 6390

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Citation Number: 62

Abstract

Three synthetic approaches towards 2, 3-substituted anthracenes are reported and discussed in terms of selectivity and viability. This allowed us to introduce a variety of substituents as sidearms. Promising results have been found using a tandem Diels-Alder aromatization reaction using 2, 3-dimethoxybutadiene 9 as a key intermediate. However, for multigram preparations the Friedel-Crafts approach is preferred.

1-Bromodecane Structure

hystazarin Structure

~86%

2,3-didecoxyanthracene-9,10-dione Structure

2,3-didecoxyant...

Phthalic anhydride Structure

Phthalic anhydride

~%

2,3-didecoxyanthracene-9,10-dione Structure

2,3-didecoxyant...

2,3-diacetoxy-9,10-anthraquinone Structure

2,3-diacetoxy-9...

~%

2,3-didecoxyanthracene-9,10-dione Structure

2,3-didecoxyant...

9,10-Anthracenedione,2,3-dimethoxy- Structure

9,10-Anthracene...

~94%

anthracene-2,3-diol Structure

anthracene-2,3-diol

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

anthracene-2,3-diol Structure

anthracene-2,3-diol

9,10-Anthracenedione,2,3-dimethoxy- Structure

9,10-Anthracene...

~85%

2,3-dimethoxyanthracene Structure

2,3-dimethoxyan...

Methyl bromide Structure

hystazarin Structure

~%

9,10-Anthracenedione,2,3-dimethoxy- Structure

9,10-Anthracene...

butane-2,3-dione Structure

butane-2,3-dione

Trimethyl orthoformate Structure

Trimethyl ortho...

~73%

2,3-Dimethoxy-1,3-butadiene Structure

2,3-Dimethoxy-1...

Phthalic anhydride Structure

Phthalic anhydride

Ethanoic anhydride Structure

Ethanoic anhydride

1,2-Benzenediol Structure

1,2-Benzenediol

~%

2,3-diacetoxy-9,10-anthraquinone Structure

2,3-diacetoxy-9...

Detail

2,3-Dimethoxy-1,3-butadiene Structure

2,3-Dimethoxy-1...

~%

2,3-dimethoxyanthracene Structure

2,3-dimethoxyan...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

2,3-dimethoxyanthracene Structure

2,3-dimethoxyan...

trimethyl(3-trimethylsilyloxybuta-1,3-dien-2-yloxy)silane Structure

trimethyl(3-tri...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~53%

2-HYDROXYANTHRAQUINONE Structure

2-HYDROXYANTHRA...

hystazarin Structure

1-Bromodecane Structure

anthracene-2,3-diol Structure

anthracene-2,3-diol

~75%

2,3-didecoxyanthracene Structure

2,3-didecoxyant...

9,10-Anthracenedione,2,3-dimethoxy- Structure

9,10-Anthracene...

~%

2,3-didecoxyanthracene Structure

2,3-didecoxyant...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

2,3-didecoxyanthracene Structure

2,3-didecoxyant...