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Original scientific paper

Hydropyrimidines. VII. Covalent Hydration and Ring Opening

V. Škarić ; Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
B. Gašpert ; Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia

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page 65-70

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The ring opening of 5,6-dihydro-4-oxo-pyrimidine (I) and its
N-methyl d erivatives II and III has been e1>tab lished as the cleavage
of the intermediary 2-hydroxytetrahydropyrimidines to 3-forma midopropionamide (VIII) and its N-methyl d e rivatives XIII and XIV.
The formation of the 2-hydroxy intermediate is proposed as the
nucleophylic addition of water to the C = N double bond of the
hydropyrimidines I-III. The rupture of 1,3 -dime thyl-5,6-dihydro-2-thioura cil (VII) procee ds to 3-(N-methyl-forma mido)-N-methylpropionamide (XV), most probably by reductive desulfurization via a carbonium ion of the mentioned type during nucleophylic addition.
The NMR spectra of formamidopropionamide are discussed.


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