Further examination of the reaction between hexahydro-N-methylcyclohept[b]indole and arenesulphonyl azides

Abstract

The reaction between 5,6,7,8,9,10-hexahydro-5-methylcyclohept[b]indole and tosyl azide in carbon tetrachloride solution yields 2,3,4,5,6,7-hexahydro-1-methyl-7-p-tolylsulphonylamino-12-p-tolylsulphonylimino-2,7-methano-1H-1-benzazonine. The compound to which this structure was previously assigned is now considered to be a derivative of octahydro-N-methylcyclohept[b]indole. p-Chlorobenzenesulphonyl azide also yields a 1H-benzazonine. The reactions of this compound have been examined and a comparison has been made with the reactions of 6-p-chlorophenylsulphonylamino-5-p-chlorophenylsulphonylimino-1,2,5,6-tetrahydro-4,6-butano-4H-pyrrolo-[3,2,1-ij]quinoline.