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Ethyl isocyanoacetate is used in the syntheses of 7-aza-tetrahydroindoles, oxazolines, benzodiazepines, imidazoles and oxazoles. For example, it is involved in the synthesis of 1H-indole-2-carboxylate by condensing with 2-bromo benzenealdehyde using CuI as a catalyst. It is a precursor used in the preparation of ethyl thiazole-4-carboxylate upon reaction with O-ethyl thioformate.
Base-catalyzed Michael addition to nitroalkenes provides a route to substituted pyrroles, valuable as intermediates for porphyrin synthesis: J. Chem. Soc., Chem. Commun., 1098 (1985); Tetrahedron, 46, 7483, 7587 (1990); Org. Synth. Coll., 9, 242 (1998).
The method has been extended to nitroaromatics, leading to pyrroles and porphyrins fused with aromatic rings: J. Chem. Soc., Perkin 1, 417 (1996).
The terminal carbon also undergoes nucleophilic attack on an acyl chloride to give an ɑ-keto imidoyl chloride, which cyclizes in base to a 2-acyl-5-ethoxy oxazole: Synth. Commun., 26, 1149 (1996).
Kondratov, I. S.; Dolovanyuk, V. G.; Tolmachova, N. A.; Gerus, I. I.; Bergander, K.; Fröhlich, R.; Haufe, G. Reactions of β-alkoxyvinyl polyfluoroalkyl ketones with ethyl isocyanoacetate and its use for the synthesis of new polyfluoroalkyl pyrroles and pyrrolidines. Org. Biomol. Chem. 2012, 10 (44), 8778-8785.
Baumann, M.; Garcia, A. M. R.; Baxendale, I. R. Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1, 2, 4-triazoles and pyrrolo-[1, 2-c] pyrimidines. Org. Biomol. Chem. 2015, 13 (14), 4231-4239.
Hazard Statements: H227-H302-H312-H332-H315-H319-H335
Combustible liquid. Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210u-P261-P280-P305+P351+P338-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.