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■ Condensation with Tetrahydropyranylurea: Synthesis of 3-Tetrahydropyranyl Uracils

F. Gómez Contreras, T. Manzano, and P. Navarro*

*Instituto de Quimica Organica General, Consejo Superior Investigaciones Cientificas, Calle Juan de la Cierva, 3, E-28006 Madrid, Spain

Abstract

The 3-tetrahydropyranyl uracil derivatives 1 and 2 have been obtained by reaction of tetrahydropyranylurea (THPU) with diethyl ethoxymethylenemalonate. The sodium salt (monohydrate) of 1 was also isolated in the same reaction. In a similar way, THPU has been condensed with ethyl ethoxymethylenecyanoacetate to give the open chain compound 3, which was identified as a mixture of the E (3a) and Z (3b) isomers. Heating of THPU with triethyl orthoformate and ethyl cyanoacetate afforded an identical mixture of isomers. By using this last procedure, the ureidoethylene derivatives of diethyl malonate, malononitrile and malonic acid (4, 5 and 6, respectively) have also been isolated and identified.