Regioselective reductions of various 3-aminosuccinimides; application to the synthesis of two heterocyclic systems

The synthesis of novel pyrrolo[3,2-c]isoquinolines is investigated starting from 3-aminosuccinimides. Various known routes leading to 3-aminosuccinimides were tested but a new approach via nucleophilic addition of arylalkylamines on maleimide gave better results. The regioselectivity of the reductio...

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Bibliographic Details
Published inTetrahedron Vol. 53; no. 6; pp. 2075 - 2086
Main Authors Brière, Jean-François, Charpentier, Patricia, Dupas, Georges, Quéguiner, Guy, Bourguignon, Jean
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.02.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
ACID
IMIDES
ANALOGS
DERIVATIVES
STEREOSELECTIVE SYNTHESIS
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Summary:The synthesis of novel pyrrolo[3,2-c]isoquinolines is investigated starting from 3-aminosuccinimides. Various known routes leading to 3-aminosuccinimides were tested but a new approach via nucleophilic addition of arylalkylamines on maleimide gave better results. The regioselectivity of the reduction of these compounds was shown to depend on the degree of substitution of the concerned 3-aminosuccinimide. The hydroxylactams are formed in-situ, then converted into the ethoxylactams. The latter, after generation of an iminium salt, afforded the target pyrroloisoquinolines and two further derivatives of another new heterocyclic system: the 3,6-methano-2,5-benzodiazocine. 3-Aminosuccinimides are obtained via nucleophilic addition of arylalkylamines on maleimide. Regioselective reduction of these compounds and in-situ generation of an iminium salt afforded the pyrrolo[3,2-c]isoquinolines 10e,f and two derivatives 9d,g of a new heterocyclic system: the 3,6-methano-2,5-benzodiazocine.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(96)01157-X