Reactions of 3-hydroxytetrahydropyrimidin-4-ones with electrophilic reagents

The reactions of nonsubstituted or 2-aryl-substituted 3-hydroxytetrahydropyrimidin-4-ones (HTHP) with carboxylic acid chlorides, tosyl chloride, or aryl isocyanates afford mainlyN,O-diacylated,N,O-ditosylated, orN,O-diarylcarbamoylated HTHP, respectively.N,O-Diacylated HTHP are also formed in the reactions of acid chlorides with Schiff's bases based on β-aminopropionohydroxamic acid.N-Acylated HTHP can be obtained by treatingN,O-diacylated HTHP with ammonia. The reactions of 2,2-dialkyl(alkylene)-substituted HTHP with acid chlorides or phenyl isocyanate giveN,O-diacylated orN,O-diphenyl-carbamoylated β-aminopropionohydroxamic acid, respectively. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2327–2332, December, 1999.