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Imino‐bridged heterocycles. III . Synthesis of mono‐bridgehead substituted 11H‐benzo[5,6]cyclohepta[1,2‐c]pyridin‐6,11‐imines by regiospecific amine to olefin cyclizations
Author(s) -
Brenner Daniel G.,
Halczenko Wasyl,
Shepard Kenneth L.
Publication year - 1985
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.5570220269
Subject(s) - chemistry , olefin fiber , imine , hydroxylamine , amine gas treating , chloroform , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Employing regiospecific amine to endocyclic olefin and hydroxylamine to exocyclic olefin cyclizations, we have developed pathways to two isomeric, bridgehead methyl‐substituted benzo[5,6]cyclohepta[1,2‐c]pyridin‐6,11‐imines. Acid catalyzed cyclization of 5 to 6 was accomplished under exceedingly mild conditions (silica gel/chloroform), whereas, thermal cyclization of 20 to generate 21 was performed analogously to the dibenzo[ a,d ]cyclohepten‐5,10‐imine system.