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Synthesis and high‐resolution 1 H NMR spectra of four dimethylaminated dipyridyl ketones
Author(s) -
Jones D. W.,
Pakdel H.,
Hallas G.,
Hepworth J. D.
Publication year - 1986
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260241010
Subject(s) - chemistry , substituent , ketone , benzene , ring (chemistry) , chloroform , nmr spectra database , proton nmr , solvent , stereochemistry , medicinal chemistry , spectral line , organic chemistry , physics , astronomy
Four new dimethylaminated pyridoylpyridine intermediates, bis(3‐dimethylamino‐2‐pyridyl) ketone (1), 6‐dimethylamino‐3‐pyridyl 4‐pyridyl ketone (2), 6‐dimethylamino‐3‐pyridyl 3‐pyridyl ketone (3) and 6‐dimethylamino‐3‐pyridyl 2‐pyridyl ketone (4), have been synthesized and their 100 MHz 1 H NMR spectra analysed iteratively as ABC, ABCX and ABXY spin systems. In 2–4 the H‐5 shift ortho to the dimethylamino substituent is unaffected by the orientation of the pyridyl substituent, but H‐4 and H‐2 are increasingly deshielded in the sequence 2–4. In 3, when benzene‐ d 6 replaces chloroform‐ d 1 as solvent, H‐5′ and H‐4′ in the unsubstituted pyridyl ring suffer appreciable upfield shifts.