Further examination of the reactions between arenesulphonyl azides and tetrahydrocarbazoles

Abstract

The nature of the product formed by treating 1-p-tolylsulphonylaminotetrahydrocarbazole with acid has been determined. 9-Methyl-4a-p-tolylsulphonylamino-2,3,4,4a-tetrahydrocarbazole has been isolated and shown to be an intermediate in the reaction of tosyl azide with 9-methyltetrahydrocarbazole. Good yields of cyclopentenoquinolines may be obtained by carrying out these reactions under basic conditions.

The products formed by heating 4a-arylsulphonylaminotetrahydrocarbazoles have been characterised, the effect of substituents at the 1-position on the nature of the product obtained when tetrahydrocarbazoles react with azides has been studied, and the kinetics of the acid-catalysed rearrangement of 1-methyl-3-p-tolylsulphonyliminoindoline-2-spirocyclopentane have been examined.