A DIRECT SYNTHESIS OF 3-(PYRROLIDIN-3-YL)INDOLES FOR USE AS CONFORMATIONALLY RESTRICTED ANALOGS OF TRYPTAMINES

Authors
MACOR JE BLANK DH RYAN K POST RJ
Citation
Je. Macor et al., A DIRECT SYNTHESIS OF 3-(PYRROLIDIN-3-YL)INDOLES FOR USE AS CONFORMATIONALLY RESTRICTED ANALOGS OF TRYPTAMINES, Synthesis, (4), 1997, pp. 443
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
4
Year of publication
1997
Database
ISI
SICI code
0039-7881(1997):4<443:ADSO3F>2.0.ZU;2-#
Abstract
An efficient, two step synthesis of 3-(pyrrolidin-3-yl)indoles 4 is de scribed. indoles react with maleimides in refluxing acetic acid afford ing 3-(indol-3-yl)succinimides 6. Reaction times and yields depend on the substituents on the indole 5. Direct reduction of the succinimides 6 with LAH affords the desired conformationally restricted tryptamine derivatives 4.