From Malonic Acid to Amide, Ester, or β-Ketoester

In this paper from Pfizer, malonic acids are reacted with carbonyl diimidazole at room temperature to generate an intermediate mono-acid imidazole which can be reacted with amines (10 examples, 85-100% yield with one failure - 1,1-cyclopropanedicarboxylic acid).  There are also individual examples of reactions with hydroxide (90%), alkoxide (91%), N,O-dimethylhydroxylamine (85%), toluenesulphonamide (79%), and ethyl potassium malonate (67% yield of β-ketoester).

 D. Lafrance,* P. Bowles, K. Leeman, and R. Rafka, Org. Lett., 2011, 13, 2322-2325.