Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-<i>b</i>]indole Core. Unusual Fragmentation with 1,2-Aryl Shift
А. В. Аксенов, Elena V. Aleksandrova, Дмитрий А. Аксенов, Anna A. Aksenova, Nicolai A. Aksenov, Mezvah A. Nobi, Michael Rubin
Abstract
Base-assisted transformations of 2-(3-oxoindolin-2-yl)acetonitriles were investigated. Unexpectedly, attempted reactions of substrates possessing nonprotected nitrogen atoms were accompanied by unusual extrusions of 2-arylacetonitriles, followed by a 1,2-aryl shift to afford 3-hydroxyindolin-2-ones. On the other hand, the reactions for N-alkyl derivatives of oxoindolines took the expected route by only providing 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles.
Topics & Concepts
ChemistryAcetonitrilesIndole testArylAlkylFragmentation (computing)StereochemistryMedicinal chemistryOrganic chemistryAcetonitrileOperating systemComputer scienceSynthesis and pharmacology of benzodiazepine derivativesSynthesis and Biological EvaluationSynthesis and Reactions of Organic Compounds