Nitrogen Bridgehead Compounds. Part  79  . Synthesis and structure elucidation of benzimidazolo[2,1‐ f ][1,6]naphthyridine aza‐derivatives | Zendy

Tóth Gábor | Zendy; Kovács Attila | Zendy; Balogh Mária | Zendy; Hermecz István | Zendy

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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.

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