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Imino‐bridged heterocycles. II . Regiospecific synthesis of the 11 H ‐benzo[5,6]cyclohepta[1,2‐ c ]pyridin‐6,11‐imine and 5 H ‐benzo[4,5]cyclohepta[1,2‐ b ]pyridin‐5,10‐imine systems
Author(s) -
Brenner Daniel G.,
Halczenko Wasyl,
Shepard Kenneth L.
Publication year - 1982
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.5570190436
Subject(s) - chemistry , sodium borohydride , imine , intramolecular force , olefin fiber , stereochemistry , amine gas treating , tricyclic , medicinal chemistry , organic chemistry , catalysis
Regiospecific synthetic pathways for two of the eight isomeric benzocycloheptapyridinimines have been developed based upon intramolecular acid catalyzed additions between an amine function and an internal olefin. The requisite amines were generated from known tricyclic ketones by ketimine formation followed by sodium borohydride reduction.