Diels−Alder Reactions of Fused Pyran-2-ones with Maleimides:  Efficient Syntheses of Benz[e]isoindoles and Related Systems

The Diels−Alder reaction of some substituted 5,6,7,8-tetrahydro-2H-1-benzopyran-2-ones (1a−f) with N-substituted maleimides (2a−c) leading to fused isoindole derivatives (5a−n, 7) or, in a few cases, to bridged double cycloadducts (fused bicyclo[2.2.2]octene derivatives) (6a−f) is presented. When X...

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Bibliographic Details
Published in:Organic letters 2003-08, Vol.5 (16), p.2833-2836
Main Authors: Kranjc, Krištof, Polanc, Slovenko, Kočevar, Marijan
Format: Article
Language:English
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Summary:The Diels−Alder reaction of some substituted 5,6,7,8-tetrahydro-2H-1-benzopyran-2-ones (1a−f) with N-substituted maleimides (2a−c) leading to fused isoindole derivatives (5a−n, 7) or, in a few cases, to bridged double cycloadducts (fused bicyclo[2.2.2]octene derivatives) (6a−f) is presented. When X = CO, the first efficient, substituent-driven aromatization of an intermediary-formed cycloadduct was observed, resulting in substituted benz[e]isoindoles (5a−k). The same type of aromatization can also be achieved in an unprecedented catalysis with Rh/C.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol034852q