Reactions of toluene-p-sulphonyl azide with derivatives of cycloheptand cyclo-oct-indole

Abstract

5,6,7,8,9,10-Hexahydrocyclohept[b]indole reacts with tosyl azide to form 6,7,8,9,10,10a-hexahydro-10a-p-tolylsulphonylaminocyclohept[b]indole (VII; n= 5) in poor yield and its N-methyl derivative yields 1-methyl-2′-p-tolylsulphonylamino-2-p-tolysulphonyliminoindole-3-spirocyclohexane (VIII; n= 4), 2,3,4,5,6,7-hexahydro-1-methyl-7-p-tolylsulphonylamino-12-p-tolylsulphonylimino-2,7-methano-1H-1-benzazepine (XI), 5-methyl-5,6,6a,7,8,9,10,10a-octahydro-10a-p-tolylsulphonylamino-6-p-tolylsulphonyliminophenanthridine (XI), and 5,6,7,8,9,10-hexahydro-5-methyl-10-p-tolylsulphonyliminocyclohept[b]indole (XXI). No 1 : 1 reaction products were isolated.

6,7,8,9,10,11-Hexahydro-5H-cyclo-oct[b]indole and its N-methyl derivative react in a similar manner to their lower homologues, although the NH derivative reacts smoothly in high yield, in contrast to its lower homologue.