Issue 0, 1979

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 2154-2161

Reactions of some indolyl alcohols and indolyl-olefins with arenesul-phonyl azides

G. A. Bahadur, A. S. Bailey, G. Costello and P. W. Scott, J. Chem. Soc., Perkin Trans. 1, 1979, 2154 DOI: 10.1039/P19790002154

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