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Diethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.
Stable equivalent of the ɑ-formylmalonate, valuable synthetic building block, particularly in heterocyclic syntheses. Review: Adv. Het. Chem., 54, (1992).
Can be converted to the unstable diethyl methylenemalonate by catalytic reduction and elimination of ethanol on distillation, see: Org. Synth. Coll., 4, 298 (1963).
Has been used for the protection of the amino group of ɑ-amino acids, allowing clean esterification by O-alkylation. The protecting group can be removed using bromine in chloroform: Synthesis, 544 (1989):
For N-protection of aminoglycosides prior to O-acetylation, see: J. Carbohydr. Chem., 14, 1133 (1995). Chlorine in chloroform at 0oC was used for deprotection.
Kim, Y. H.; Kim, H. J.; Shin, J. H.; Bhatia, S. K.; Seo, H. M.; Kim, Y. G.; Lee, Y. K.; Yang, Y. H.; Park, K. Application of diethyl ethoxymethylenemalonate (DEEMM) derivatization for monitoring of lysine decarboxylase activity. J. Mol. Catal. B: Enzym. 2015, 115, 151-154.
Megias, C.; Giraldo, I. C.; Calle, J. G.; Vioque, J.; Alaiz, M. Determination of l-canavanine and other free amino acids in Vicia disperma (Fabaceae) seeds by precolumn derivatization using diethyl ethoxymethylenemalonate and reversed-phase high-performance liquid chromatography. Talanta 2015, 131, 95-98.
Gefahrenhinweise (EU): H303-H315-H319-H334-H317
May be harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause an allergic skin reaction.
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