When reacting with I-2, 2-(cyclopent-2-enyl)anilines undergo cyclization in
to 3-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles in high yields. The m
inor reaction products were 3,5- or 3,7-diiodoindolines. Ammonolysis of 3-i
odo-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole or its N-chloroacet
yl derivative results in 3-amino-5-methyl-1,2,3,3a,4,8b-hexahydro- and 5-me
thyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles.