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Cyclopenta[ a ]quinolizine: A Novel Pseudoazulene with a Bridgehead Nitrogen Atom
Author(s) -
Gormay Pavel V.,
Rybakov Victor B.,
Babaev Eugene V.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000753
Subject(s) - chemistry , pyridinium , nitrogen atom , ring (chemistry) , delocalized electron , pyridinium compounds , atom (system on chip) , nuclear magnetic resonance spectroscopy , computational chemistry , crystallography , stereochemistry , medicinal chemistry , organic chemistry , computer science , embedded system
Cyclopenta[ a ]quinolizine, a novel tricyclic pseudoazulene, was prepared by reaction of cyclopentadienyllithium with oxazolo[3,2‐ a ]pyridinium or substituted pyridinium salts. Structural analysis (X‐ray analysis, NMR and UV spectroscopy) and DFT calculations confirm its highly dipolar nature (due to delocalization of the negative charge around the five‐membered ring) combined with partial localization of bonds in both six‐membered rings.