The High Pressure Diels-Alder Reactions of 5-Methoxy-2-methyl-4-(p-nitrophenyl)oxazole with Ethylenic Dienophiles

Article abstract of DOI:10.1246/bcsj.59.3197

The high pressure Diels-Alder reactions of 5-methoxy-2-methyl-4-(p-nitrophenyl)oxazole with ethylenic dienophiles such as N-methylmaleimide, N-phenylmaleimide, dimethyl maleate and dimethyl fumarate gave the corresponding adducts in good to excellent yields.The effects of pressure, temperature, solvents on the yields were investigated.The high pressure also increased the formation of 3-hydroxypyridine derivatives via the elimination of methanol from the adducts.The stereospecificity of the reaction was confirmed for the reactions with maleate and fumarate.