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Synthesis of spirocyclic indolines by interruption of the Bischler-Napieralski reaction.

ABSTRACT: The development of a versatile method for the synthesis of spirocyclic pyrrolidinoindolines is discussed. Treatment of N-acyltryptamines with trifluoromethanesulfonic anhydride-2-chloropyridine reagent combination affords highly persistent spiroindoleninium ions that are subject to intra- and intermolecular addition at C2 by nucleophiles.

SUBMITTER: Medley JW

PROVIDER: S-EPMC3779471 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Synthesis of spirocyclic indolines by interruption of the Bischler-Napieralski reaction.

Medley Jonathan William JW Movassaghi Mohammad M

Organic letters 20130705 14

The development of a versatile method for the synthesis of spirocyclic pyrrolidinoindolines is discussed. Treatment of N-acyltryptamines with trifluoromethanesulfonic anhydride-2-chloropyridine reagent combination affords highly persistent spiroindoleninium ions that are subject to intra- and intermolecular addition at C2 by nucleophiles. ...[more]

PMID: 23829389

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