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Stereoselective synthesis of conformationally constrained tropane analogues: 6‐Chloro‐2,5‐diazatetracyclo[8.5.0.0 2,13 .0 4,9 ]pentadeca‐4,6,8‐triene‐11‐one and 6‐chloro‐2,7‐diazatetracyclo‐[8.5.0.0 2,13 .0 4,9 ]pentadeca‐4,6,8‐triene‐11‐one
Author(s) -
Cheng Jie,
Xu Liang,
Stevens Edwin D.,
Trudell Mark L.,
Izenwasser Sari,
Wade Dean
Publication year - 2004
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.5570410414
Subject(s) - chemistry , tropane , tricyclic , intramolecular force , stereoselectivity , stereochemistry , intramolecular reaction , nicotinic agonist , bicyclic molecule , catalysis , receptor , organic chemistry , biochemistry
Two conformationally constrained tropane derivatives were prepared as rigid nicotinic acetylcholine receptor ligands. A palladium catalyzed intramolecular α‐arylation reaction was employed to generate the tricyclic compounds in good yields from N ‐(bromo‐chloropyridylmethyl)‐8‐azabicyclo[3.2.1]octan‐3‐ones.