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Tetronic acid is used as a precursor of a variety of substituted and ring-fused furans and butenolides. It is an acidic building block for heterocyclic compounds for medicinal applications. It is used for selective O-alkyaltion reactions involving cesium fluoride. It is also used to prepare 3H-furo[3,4-b]quinolin-1-one by reacting with 2-amino-benzaldehyde.
Equivalent to the -lactone of 4-hydroxyacetoacetic acid.
Selective O-alkylation is promoted by CsF under mild conditions: Synlett, 843 (1995).
Versatile precursor of a variety of substituted and ring-fused furans and butenolides; see, e.g.: J. Org. Chem., 48, 1914 (1983); Synthesis, 155 (1996).
Li, X. K.; Xiong, F.; Shen, Z. Y.; Zhang, S. P.; Zhou, Y. H.; Xu, M. L.; Zhou, Z. Q. Unexpected Facile Synthesis of Tetronic Acid During the Research on Stereospecific Total Synthesis of (+)-Biotin Starting from D-Erythorbic Acid as Chiral Pool. Asian J. Chem. 2015, 27 (5), 1957.
Chopin, N.; Yanai, H.; Likawa, S.; Pilet, G.; Bouillon, J. P.; Médebielle, M. A Rapid Entry to Diverse gamma-Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived gamma-Lactones and Metal-Catalyzed Postfunctionalization. Eur. J. Org. Chem. 2015, 2015 (28), 6259-6269.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant