Synthesis Of Heterocyclic Compounds By Dimethyl Methoxymethylenemalonate

The heterocyclic compounds including pyrazole,isoxazole and pyrimidine usually have good biological activeties.Diethyl ethoxymethylenemalonate and N,N-dimethyl-amino-methylenemalonate were replaced by dimthyl methoxymethylenemalonate(DMMM)with less molecular weight and better atom economical efficiency.The following compounds were prepared by DMMM and nucleophilic reagents:5-hydroxyl-4-pyrazole methyl formate,1-phenyl-5-hydroxyl-4-pyrazole methyl formate,5-hydroxyl isoxazole-4-methyl formate,2,4-hydroxyl-5-pyrimidine methyl formate and 2-methylthio-4-hydroxyl-5-pyrimidine methyl formate.The conditions were optimized and better process parameters were gained.These researches were not reported before.They had good economic and applied values.5-Hydroxyl-4-pyrazole methyl formate was synthesized by DMMM and hydrazine hydrate.The molar ratio was 1:1.2.They reacted at 80? for 4 hours using ethanol and water as solvent.The purity of 5-hydroxyl-4-pyrazole was 99%,and the yield was 82%.1-Phenyl-5-hydroxyl-4-pyrazole methyl formate was synthesized by DMMM and hydrochloride benzene hydrazine.The molar ratio was 1:1.05.They reacted at reflux temperature for 5 hours using ethanol as solvent.The purity of product was 98%,and the yield was 66.5%.5-Hydroxyl isoxazole-4-methyl formate was synthesized by DMMM and hydroxylamine hydrochloride.The molar ratio was 1:1.2.They reacted for 40 minute.The purity of product was 98%,and the yield was 50.7%.2,4-Hydroxyl-5-pyrimidine methyl formate was prepared by DMMM and urea.The molar ratio was 1:1.2.They reacted at 95 ? for 3 hours.The purity of product was 98%,and the yield was 31.5%.2-Methylthio-4-hydroxyl-5-pyrimidine methyl formate was prepared by DMMM and 2-methyl-2-thiopseudourea sulfate.The molar ratio was 1:1.1.They reacted at room temperature for 3 hours.The purity of product was 98%,and the yield was 52.9%.