Reactions of 1,3,4,5-tetrahydro-5-methylthiopyrano[4,3-b]indole, of 1,2,6,7,8,9-hexahydropyrrolo[3,2,1-jk]carbazole, and of 1,2,7,8,9,10-hexhydro-6H-cyclohepta[b]pyrrolo[3,2,1-hi]indole with arenesulphonyl azides

Abstract

Arenesulphonyl azides react with N-methyltetrahydrothiopyrano[4,3-b]indole yielding derivatives of 3-iminoindoline-2-spirothiacyclopentane and of 2-iminoindoline-3-spirothiacyclopentane in poor yield. With hexahydropyrrolo[3,2,1-jk]carbazole the azides gave 2-arylsulphonylamino-2-(indolin-7-yl)cyclohexanones, arylsulphonyliminotetrahydropyrrolo[3,2,1-hi]indolespirocyclopentanes, and derivatives of cyclopenta[c]pyrrolo-[3,2,1-ij]quinoline. Hexahydro-6H-cyclohepta[b]pyrrolo[3,2,1-hi]indole afforded derivatives of pyrrolo[3,2,1-de]phenanthridine and, in good yield, 6-arylsulphonylamino-5-arylsulphonylimino-1,2,5,6-tetrahydro-4,6-butano-4H-pyrrolo[3,2,1-ij]quinolines. The chemistry of these last-named compounds has been examined.