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Synthesis of bridgehead nitrogen heterocycles
Author(s) -
Scovill John P.,
Burckhalter Joseph H.
Publication year - 1980
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.5570170105
Subject(s) - chemistry , sodium borohydride , acetic acid , catalysis , nitrogen , organic chemistry , catalytic hydrogenation , palladium , carbon fibers , materials science , composite number , composite material
Reductive cyclizations of N ‐[2‐(2‐pyridyl)ethyl]imides were accomplished by employing a palladium on carbon catalyst in ethanolic acetic acid as the hydrogenation medium. Reduction of the corresponding N ‐[2‐(2‐quinolyl)ethyl]imides ceased at the 1,2,3,4‐tetrahydroquinolyl stage. Controlled reduction of the tetrahydroquinolyl imides with sodium borohydride gave amido alcohols which afforded bridgehead nitrogen heterocycles upon cyclodehydration.