Isoquinoline SrnI reaction

Although the intramolecular SrnI reaction has been studied to a lesser extent as compared to the intermolecular process, it has been shown to represent a highly useful route for the synthesis of various heterocyclic compounds. For example, the SrnI cyclization of N-alkyl-N-acyl-o-haloaniUnes and N-acyl-N-methyl-o-chlorobenzylamines (Equation 13.5) gives N-aUcylindol-2-one and 1,4-dihydro-2H-isoquinolin-3-ones in moderate to good yields [21]. lodoketone 1 reacts under SrnI conditions to provide the complex heterocyclic compound 2 with excellent yield (Equation 13.6) [22]. 

Biologically important heteroarenes are readily prepared by the reaction of ketone, ester or amide enolates with ortho-substituted aryl halides [11]. The ortho-substituent can subsequently be used for further synthetic manipulations. For example, the reaction of o-iodo or o-bromoaniline with enolates generated from aliphatic or aromatic ketones under SrnI conditions provides 2,3-disubstituted indoles in moderate to excellent yields (Equation 13.2) [12, 13]. 2,3-Disubstituted isoquinolin-l-ones (Equation 13.3) and isoquinolines are readily prepared using o-iodobenzamide and o-iodobenzylamine as radical precursors by the same approach [14]. 

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