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Studies on the syntheses of heterocyclic compounds. Part DLXXXII . Synthesis of benzo[ a ] quinolizine derivatives and pyrrolo[2,1‐ a ] isoquinoline derivatives by phenolic cyclization
Author(s) -
Kametani Tetsuji,
Kigasawa Kazuo,
Hüragi Mineharu,
Ishimaru Hazuhide,
Haga Seiji
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110631
Subject(s) - isoquinoline , chemistry , aluminum hydride , phenethylamine , lithium aluminium hydride , lactam , organic chemistry , stereochemistry , catalysis , methoxide
Phenolic cyclization of 3‐hydroxy phenethylamine with acylbutyric acid and acylpropionic acid afforded the lactam of the corresponding benzol[ a ] quinolizine and pyrrolo[2, 1‐ a ]isoquinoline derivatives, which were reduced with lithium aluminum hydride to give the benzol[ a ]quinolizine and pyrrolo[2,1 ‐ a ] isoquinoline derivatives, respectively. The configurations of acetyl derivatives of these products were determined.