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

Gábor Tóth, Attila Kovács, Mária Balogh, I. Hermecz

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Abstract

6‐Substituted 1,6‐naphthyridine‐5(6H)‐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(6H)‐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 1H and 13C nmr assignment was achieved by different 2D carbon‐proton correlation measurements.

Original languageEnglish
Pages (from-to)497-501
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume28
Issue number2
DOIs
Publication statusPublished - 1991

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ASJC Scopus subject areas

  • Organic Chemistry

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