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DOI: 10.1055/s-0034-1379110
Manganese(III) Acetate Mediated Oxidative Free-Radical Reactions of 2-(Alkenylamino)-1,4-naphthoquinones with 1,3-Dicarbonyl Compounds
Publication History
Received: 29 July 2014
Accepted: 19 August 2014
Publication Date:
24 September 2014 (online)
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Abstract
The manganese(III)-mediated oxidative free-radical reactions of 2-(alkenylamino)-1,4-naphthoquinones are described. The free-radical reaction of 2-(allylamino)-1,4-naphthoquinone with 1,3-dicarbonyl compounds provides a novel method for the synthesis of benzo[f]indole-4,9-diones and benzo[g]quinoline-5,10-diones. The reaction shows high chemoselectivity, depending on the solvents and 1,3-dicarbonyl compounds used. With both 1,3-diones and β-keto esters, in acetic acid, the condensation products, benzo[f]indoles, were generated selectively; in acetonitrile, the [5+1]-cyclization products, benzo[g]quinolines and tetrahydrobenzo[g]quinolines, were produced in high chemoselectivity. With diethyl malonate, the [5+1]-cyclization product, the corresponding tetrahydrobenzo[g]quinoline, was produced exclusively. The free-radical reaction of a 2-(vinylamino)-1,4-naphthoquinone with 1,3-dicarbonyl compounds produced benzo[g]quinolines effectively.
Key words
manganese(III) acetate - free radicals - 2-(alkenylamino)-1,4-naphthoquinones - 1,3-dicarbonyl compounds - solvent effectsSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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