Concise synthesis of tetrahydro derivatives of the pyrido[2,3- b]acridine and pyrido[3,2- b]acridine ring systems

5,6,7,8-Tetrahydro-1,4-acridinequinones were readily prepared by Friedländer reaction between cyclohexanone and 2-amino-3,6-dimethoxybenzaldehydes or 2-amino-3,6-dimethoxyacetophenones, followed by oxidative demethylation. Their Diels-Alder reactions with 1-dimethylamino-1-azadienes gave pyrido[3,2-...

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Bibliographic Details
Published in:Tetrahedron 1999-10, Vol.55 (43), p.12637-12646
Main Authors: Blanco, M adel Mar, Avendaño, Carmen, Menéndez, J.Carlos
Format: Article
Language:English
Subjects:
acridines
Diels-Alder reactions
Marine metabolites
quinolines
quinones
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Summary:5,6,7,8-Tetrahydro-1,4-acridinequinones were readily prepared by Friedländer reaction between cyclohexanone and 2-amino-3,6-dimethoxybenzaldehydes or 2-amino-3,6-dimethoxyacetophenones, followed by oxidative demethylation. Their Diels-Alder reactions with 1-dimethylamino-1-azadienes gave pyrido[3,2- b]acridines in a regioselective fashion. The regiochemistry of the cycloaddition could be inverted through the introduction of a bromine atom at the C-5 position, to give pyrido[2,3- b]acridines. The latter ring system is a structural fragment common to several polyciclic marine natural products with antitumour properties, including ascididemin, eilatin and biemnadin. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00738-3