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- W2000980764 abstract "6-Methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones 1-5 were subjected to Vilsmeier-Haack acylation with complexes of phosphoryl chloride and different amides. Acylation at position 9 of the pyridopyrim-idines was successful with the iminium salt formed in situ from N-formylpiperidine, N-methylformanilide or N,N-diethylbenzamide, but unsuccessful with the iminium salt formed from N,N-diethylacetamide or N,N-di-ethylisobutyramide, respectively. The iminium salt formed from formanilide, N-methylpyrrolidinone or formamide reacted only with those tetrahydropyridopyrimidinones which contain a strongly electronegative substituent (e.g. CN or CO2Et) in position 3. With the latter derivatives, the 9-phenylaminomethylene group could be introduced using N,N-diphenylformamide or in a “one-pot” procedure with aniline and triethyl orthoformate. Ethanolysis of 9-N-methyl-N-phenylaminomethylene derivatives 15 and 19 afforded 9-ethoxy-methylene compounds 26 and 27 in the presence of hydrogen chloride. The structures of the 9-substituted 6-methyltetrahydropyridopyrimidin-4-ones 14-25 were elucidated by means of uv, 1H and 13C nmr spectroscopy. 9-Piperidinomethylene 14, 9-(N-methyl-N-phenylaminomethylene 15-19 and 9-(N-methyl-2-pyrrolidinylidene) 21 derivatives exist as E geometric isomers. 9-Phenylaminomethylene-6-methyl-4-oxo-6,7,8,9-tetra-hydro-4H-pyrido[1,2-a]pyrimidine-3-carbonitrile 20 displays a solvent-dependent E-Z isomerism. The bis-compound 25 contains both E and Z geometric exo C CH double bonds. 9-Benzoyl derivatives 23 and 24 exist predominantly as the 1,6,7,8-tetrahydropyridopyrimidin-4-one tautomer." @default.
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- W2000980764 title "Nitrogen bridgehead compounds. Part<b>50</b>. Vilsmeier-haack acylation of 6,7,8,9-tetrahydro-4<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidin-4-ones, Part 5" @default.
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- W2000980764 doi "https://doi.org/10.1002/jhet.5570220302" @default.
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