Simple Aza-Conjugate Addition Methodology for the Synthesis of Isoindole Nitrones and 3,4-Dihydroisoquinoline Nitrones

Lucy R. Peacock, Robert S. L. Chapman, Adam C. Sedgwick, Mary F. Mahon, Dominique Amans, Steven D. Bull

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

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 hydrox-ylamine, enamine and amine derivatives. Isoindole nitrones react with dimethyl acetylenedicarboxylate (DMAD) via a [4+2]-cycloaddition/deamination pathway to afford substituted naphthalene derivatives, whilst 3,4-dihydroisoquinoline nitrones react with DMAD via a [1,3]-dipolar cycloaddition pathway to afford tricyclic heteroarenes
Original languageEnglish
Pages (from-to)994-997
JournalOrganic Letters
Volume17
Issue number4
Early online date11 Feb 2015
DOIs
Publication statusPublished - 20 Feb 2015

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