The Reaction of D-Arabinopyranosylurea with Malononitrile and Triethyl Orthoformate

Abstract Three-component coupling of arabinosylurea (or its triacetyl derivative), malononitrile and triethyl ortho-formate affords 1-(α-D-arabinopyranosyl)-ureidomethylene-malononitriles. These compounds in the presence of triethylamine undergo cyclization to give 2-oxo-4-imino-5-cyano-3-(α-D-arabinopyranosyl)-2,3,4,5-tetrahydropyrimidines. The pyranose structure of arabinosylurea was demonstrated by X-ray analysis. The synthesized compounds were studied by 1H, 13C NMR spectroscopy.