Synthesis of hydroisoindoles via intramolecular Diels–Alder reactions of functionalised amido trienes

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Abstract
Reactions of amino dienes with acryloyl chloride, malefic anhydride, bromomaleic anhydride, and dichloromaleic anhydride were studied. Acylation and Intramolecular reaction by Diels–Alder cyclisation gave bicyclic adducts. Adducts of dichloromaleic anhydride readily underwent dechlorodecarboxylation to give either conjugated or non-conjugated dienes. By studying related cyclisations with other dienophiles, the relative preference for formation of either cis- or trans-fused bicyclic adducts was determined. The dehydrochlorination, the reductive dechlorination, and the hydrogenation of certain adducts is reported.

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