Synthesis of 3-substituted cyclopenta[b]indoles

Citation
Rr. Gataullin et al., Synthesis of 3-substituted cyclopenta[b]indoles, RUSS CHEM B, 49(10), 2000, pp. 1767-1770
Citations number
14
Categorie Soggetti
Chemistry
Journal title
RUSSIAN CHEMICAL BULLETIN
ISSN journal
10665285 → ACNP
Volume
49
Issue
10
Year of publication
2000
Pages
1767 - 1770
Database
ISI
SICI code
1066-5285(200010)49:10<1767:SO3C>2.0.ZU;2-F
Abstract
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.