Attempted Heterocyclic Syntheses Through Electrophilic Ring Closure Reactions of 2-Allylaniline Systems Containing Larger Side Chains

Abstract

The electrophile-initiated cyclization of some 2-allylanilines and their amide derivatives has been further investigated. Although 2-allylanilines with small, allylic substituents such as methyl reacted with iodine to yield 3-iodo-1,2,3,4-tetrahydroquinolines the 2-allylanilines with larger substituents related to those of virantmycin provided low yields of the tetrahydroquinoline as part of a complex product mixture.