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Nitrogen Bridgehead Compounds. Part 79 . Synthesis and structure elucidation of benzimidazolo[2,1‐ f ][1,6]naphthyridine aza‐derivatives
Author(s) -
Tóth Gábor,
Kovács Attila,
Balogh Mária,
Hermecz István
Publication year - 1991
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.5570280257
Subject(s) - chemistry , nitrogen , yield (engineering) , phosphoryl chloride , ring (chemistry) , spectroscopy , nuclear magnetic resonance spectroscopy , carbon fibers , medicinal chemistry , stereochemistry , organic chemistry , composite number , materials science , physics , quantum mechanics , metallurgy , composite material
6‐Substituted 1,6‐naphthyridine‐5(6 H )‐ones were prepared from diethyl 2‐[2‐(dimethylamino)vinyl]‐6‐methylpyridine‐3,5‐dicarboxylate 1 [2] by ring closure with aromatic and heteroaromatic diamines ( o ‐phenylenediamine, 2,3‐diaminopyridine, 3,4‐diaminopyridine and 4,5‐diaminopyrimidine, respectively). 1,6‐Naphthyridine‐5(6 H )‐ones were cyclised in phosphoryl chloride to yield nitrogen bridgehead tetracycles 6‐9 . The structure of the products was established by nOe difference spectroscopy. A complete 1 H and 13 C nmr assignment was achieved by different 2D carbon‐proton correlation measurements.