Reactions of some 1,3-disubstituted indoles and of 3-methylindole with arylsulphonyl azides

Abstract

1,3-Dimethylindole reacts with arylsulphonyl azides forming 1,3-dimethyl-2-arylsulphonylaminoindoles. The compounds exist in solution as both the aminoindole and iminoindoline forms. The reaction of 1-benzyl-3-methyl-indole is similar but 1-methyl-3-phenylindole is less reactive and yielded crystalline material with only one azide. 1,3-Dimethylindole and 3-methylindole react with tosyl azide in the presence of pyridine forming compounds which contain two tolylsulphonyl groups.