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Ethyl nitroacetate has been used in the synthesis of γ-oxoacids via Michael addition reaction with α,β-unsaturated ketones, fuctionalization of C4-position on pyrimidine and C6-position on 2?-deoxyguanosine to produce novel nucleosides, facile synthesis of α,α-diisobutylglycine, synthesis of DL-4,4-difluoroglutamic acid. It is also used as an intermediate in the preparation of unsubstituted amino acids.
Maialen Aginagalde, et al. Formation of γ-oxoacids and 1H-pyrrol-2(5H)-ones from α,β-unsaturated ketones and ethyl nitroacetate.J. Org. Chem.,2010,75(21), 7435-8.
Victor Timoshchuk. Functionalization of pyrimidine and purine nucleosides at C4 and C6: C-nucleophilic substitution of their C4- and C6-(1,2,4-triazol-1-yl) derivatives.Nucleosides Nucleotides Nucleic Acids.,2005,24(5-7), 1043-1046.
In the presence of the Mitsunobu reagent (PPh3/DEAD) oxidizes alcohols to carbonyl compounds: Tetrahedron Lett., 22, 2295 (1981).
Reacts with 2,3-epoxyaldehydes to give 3-ethoxycarbonyl-4-hydroxy-5-(1-hydroxyalkyl)-2-isoxazoline-2-oxides: J. Org. Chem., 55, 781 (1990):
Similarly, reaction with ɑ-bromo enones gives 5-acyl-3-(ethoxycarbonyl)-2-isoxazoline-2-oxides by a tandem conjugate addition - ring closure: J. Org. Chem., 60, 6624 (1995).
Conjugate addition to various enones, followed by reductive cyclization with Formamidinesulfinic acid, A11885, provides a convenient new route to pyrroles: Tetrahedron Lett., 36, 9469 (1995). For examples with reaction schemes, see 2-Benzylidenecyclohexanone, L13434 and 3-Penten-2-one, L13031.
For a review of the use of nitroacetic acid and its esters in organic synthesis, see: Synthesis, 666 (1979).
Gefahrenhinweise (EU): H227-H315-H319
Combustible liquid. Causes skin irritation. Causes serious eye irritation.
Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.