Syntheses and NMR, MS and X-ray Investigations of Homoadamantane-fused Pyridopyrimidinones

Zsuzsanna Cs Gyarmati, Péter Csomós, Gábor Bernáth, Pauliina Valtamo, Henri Kivelä, Gyula Argay, Alajos Kálmán, Karel D. Klika, Kalevi Pihlaja

Research output: Article

4 Citations (Scopus)

Abstract

The reactions of ethyl 5-oxotricyclo[4.3.1.1 3,8]undecane-4-carboxylate (2) with methyl-substituted 2-aminopyridines in polyphosphoric acid (PPA) gave two products, linearly-condensed pyridopyrimidinones 4a-c and 2-pyridylcarboxamides 5a-c, whereas the reactions with amino, hydroxy and nitro derivatives of 2-aminopyridine furnished only linearly-condensed pyridopyrimidinones (4g-j). Use of a mixture of PPA and phosphorus oxychloride as solvent afforded both linearly- (4a-c,e,f) and angularly-condensed (6a-c,e,f) pyridopyrimidinones. In toluene, with p-toluenesulfonic acid as catalyst, 2-pyridylcarboxamides 5a-f were obtained. In a mixture of PPA and phosphorus oxychloride at 80-120 °C, 5a-f yielded angularly-condensed pyridopyrimidinones 6a-f. All the products exhibited characteristic features, as determined by NMR and electron ionization mass spectrometry and X-ray crystallography.

Original languageEnglish
Pages (from-to)187-199
Number of pages13
JournalJournal of Heterocyclic Chemistry
Volume41
Issue number2
DOIs
Publication statusPublished - jan. 1 2004

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ASJC Scopus subject areas

  • Organic Chemistry

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