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

Org Lett

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.

Published: July 2013

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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3779471PMC
http://dx.doi.org/10.1021/ol401465yDOI Listing

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