Reactions with arenesulphonyl azides of some indoles with oxygen- and nitrogen-containing substituents

Abstract

Treatment of 2,3,4,5-tetrahydro-5-methyl-2-tosyl-1H-pyrido[4,3-b]indole with p-nitrobenzenesulphonyl azide affords 1-methyl-2-p-nitrophenylsulphonylimino-1′-tosylindoline-3-spiro-3′-pyrrolidine in moderate yield: 1,3,4,5-tetrahydro-5-methylpyrano[3,4-b]indole reacts with p-chlorobenzenesulphonyl azide to form 3-p-chlorophenyl-sulphonylimino-1-methylindoline-2-spiro-3′-tetrahydrofuran. The reaction of methyl 1,3-dimethylindole-2-carboxylate with p-nitrobenzenesulphonyl azide involves migration of the methoxycarbonyl group.

From the reaction of methyl 1,3-dimethylindol-2-ylacetate with azides derivatives containing the 2-methyleneindoline nucleus have been isolated.