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The synthesis of 1,4‐ethano‐1,2,3,4‐tetrahydroisoquinolines as rigid analogues of adrenergic agents
Author(s) -
Muellner Frank W.,
Bauer Ludwig
Publication year - 1983
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.5570200629
Subject(s) - chemistry , tetrahydroisoquinoline , tricyclic , aluminum hydride , adduct , lithium (medication) , lactam , catalysis , reduction (mathematics) , lithium aluminium hydride , hydride , medicinal chemistry , aryne , stereochemistry , 2 pyridone , organic chemistry , medicine , geometry , mathematics , methoxide , endocrinology , hydrogen
The Diels‐Alder addition of benzyne and 4,5‐dimethoxybenzyne to 1‐(2‐ trans ‐phenylvinyl)‐2‐pyridone and 1‐benzyl‐3‐benzyloxy‐2‐pyridones provided members of the 1,4‐etheno‐3‐oxo‐1,2,3,4‐tetrahydroisoquinoline system. Catalytic reduction of these adducts yielded the corresponding tricyclic lactams. Lithium aluminum hydride reduction of these lactams produced a number of 1,4‐ethano‐1,2,3,4‐tetrahydroisoquinolines.