Reactions of some indolyl alcohols and indolyl-olefins with arenesul-phonyl azides
Abstract
The reactions of 1, 3-dimethylindol-2-ylmethanols with arenesulphonyl azides afford 2-arenesulphonylamino-1, 3-dimethylindoles as the major products, the side chain being lost, whilst hexahydro-5-methylcyclohept[b]indol-6-ol yields 2-arenesulphonylimino-2′-hydroxy-1-methylindoline-3-spirocyclohexanes. From the reaction between 5-methyl-5, 8, 9, 10-tetrahydrocyclohepta[b]indole and p-chlorobenzenesulphonyl azide three products have been isolated and shown to be 2-p-chlorophenylsulphonylimino-1-methylindoline-3-spirocyclohex-2′-ene, 6-p-chlorophenylsulphonylimino-5, 6, 7, 8, 9, 10-hexahydro-5-methylcyclohepta[b]indole and 2′-p-chlorophenylsulphonylaminomethylene-2-p-chlorophenylsulphonylimino-1-methylindoline-3-spirocyclopentane.