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  • Title: Simple aza-conjugate addition methodology for the synthesis of isoindole nitrones and 3,4-dihydroisoquinoline nitrones.
    Author: Peacock LR, Chapman RS, Sedgwick AC, Mahon MF, Amans D, Bull SD.
    Journal: Org Lett; 2015 Feb 20; 17(4):994-7. PubMed ID: 25671494.
    Abstract:
    Aryl-aldehydes containing ortho-substituted α,β-unsaturated carboxylic acid derivatives react with hydroxylamine to afford reactive N-hydroxy-carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford isoindole nitrones and 3,4-dihydroisoquinoline nitrones in good yield. Conditions have been developed to reduce these isoindole nitrones to their corresponding hydroxylamine, enamine, and amine derivatives. Isoindole nitrones react with dimethyl acetylenedicarboxylate (DMAD) via a [4 + 2]-cycloaddition/deamination pathway to afford substituted naphthalene derivatives, while 3,4-dihydroisoquinoline nitrones react with DMAD via a [1,3]-dipolar cycloaddition pathway to afford tricyclic heteroarenes.
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