The reactions of toluene-p-sulphonyl azide with 2,3-dimethylindole, 1,2,3-trimethylindole, tetrahydrocarbazole, and 9-methyltetrahydrocarbazole

Abstract

Toluene-p-sulphonyl azide reacts with 2,3-dimethylindole forming a 3-p-tolylsulphonylamino-3H-indole, with 1,2,3-trimethylindole to form 1,3-dimethyl-3-p-tolylsulphonylamino-2-p-tolylsulphonyliminoindoline and 1,3-dimethyl-2-p-tolylsulphonyliminomethylindole, and with tetrahydrocarbazole to form 4a-p-tolysulphonylamino-2,3,4,4a-tetrahydro-1H-carbazole. From the reaction with 9-methyltetrahydrocarbazole five compounds were isolated: 1-methyl-3-p-tolysulphonyliminoindoline-2-spirocyclopentane, 9-methyl-1-p-tolylsulphonylamino-tetrahydrocarbazole, 5-methyl-9b-p-tolysulphonylamino-4-p-tolylsulphonylimino-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline, 5-methyl-4-p-tolysulphonylimino-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinoline, and 1-methyl-2′-p-tolylsulphonylamino-2-p-tolyslsulphonyliminoindoline-3-spirocyclopentane.