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Construction of tetracyclic indole bases via Aza Diels‐Alder reaction of indolylethylimines with Brassard's diene
Author(s) -
Lock Ralf,
Waldmann Herbert
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.15619940511
Subject(s) - tryptamine , chemistry , iminium , indole test , diene , tryptamines , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , natural rubber
Schiff's bases 3 derived from tryptamine react with Brassard's diene 4 in the presence of EtAlCl 2 to give functionalized 1,2,5,6‐tetrahydropyridines which are subsequently transformed to indolo[2,3‐ a ]quinolizines 8–10 by the Bischler‐Napieralski reaction and reduction of the intermediate iminium salts with NaBH 4 .