Beilstein J. Org. Chem.2024,20, 243–253, doi:10.3762/bjoc.20.24
pyridine rings, the naphthalene core at positions 5(8) and the CH2CH2 bridge (dehydrogenation) undergo chemical modifications under mild conditions, giving the corresponding acenaphthylenes. The latter can also be obtained in an unusual way by tele-elimination from 5,8-dibromodipyridoacenaphthene by
reaction with neutral or anionic bases.
Keywords: dipyrido[3,2-e:2′,3′-h]acenaphthene (acenaphthylene); hydrogen bonding; π-stacking; substitution reactions; tele-elimination; Introduction
Quinoline derivatives, classical nitrogen-containing heterocycles, are widely distributed in nature in various forms
be more basic than diamine 1, the cumulative effect of all functional groups in this compound led to a slight drop in the pKa value compared to quinoquinolines 3 and 5, despite the presence of two electron-donating methoxy groups.
Bromination and tele-elimination
As preliminary experiments showed
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Graphical Abstract
Scheme 1:
Comparison of basicity (in water scale) and synthetic availability of quinoline-type azaarenes and ...