REACTIONS OF SOME INDOLYL ALCOHOLS AND INDOLYL-OLEFINS WITH ARENESULFONYL AZIDES

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.