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Synthesis and structural determination of 5 H ‐benzocyclohepten‐5,8‐imines
Author(s) -
Dicesare John C.,
Burgess Jason P.,
Mascarella S. Wayne,
Carroll F. Ivy,
Rothman Richard B.
Publication year - 1994
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.5570310131
Subject(s) - chemistry , triethylamine , tetrahydrofuran , acetonitrile , ring (chemistry) , iodide , imine , methyl iodide , stereochemistry , medicinal chemistry , organic chemistry , catalysis , solvent
Treatment of 4‐hydroxy‐ N ‐methylisoquinolinium iodide with triethylamine in tetrahydrofuran or acetonitrile forms 2‐methyl‐4‐oxidoisoquinolinium ( 2 ) in situ. Once formed, 2 can be trapped with dipolarophiles possessing varying degrees of activation to form the 5 H ‐benzocyclohepten‐5,8‐imine ring system. Various 2‐D nmr experiments were used in the identification of the stereochemical and regiochemical assignments for the ring system.