title: 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.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
authors.forename: Jonathan William
authors.initials: JW
authors.lastname: Medley
authors.forename: Mohammad
authors.initials: M
authors.lastname: Movassaghi
mesh_terms: D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D007211:Indoles; D011759:Pyrrolidines; D013141:Spiro Compounds; C057812:indoline