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Paper | Regular issue | Vol 32, No. 11, 1991, pp.2205-2215
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5845
Tin (IV) Chloride-promoted Reactions of α-Hydroxy Nitriles with β-Dicarbonyl Compounds Synthesis of 4-Amino-2,5-dihydro-2-furanones and Their Conversion into Tetronic Acid Derivatives

Augusto C. Veronese,* Rosella Callegari, and Antonella Bertazzo

*Dipartimento di Scienze Farmaceutiche, Università degli Studi di Ferrara, Via Scandiana 21 di Mortara 17-19, I-44100 Ferrara, Italy

Abstract

β-Keto esters and β-diesters react with α-hydroxy nitriles in the presence of stoichiometric amounts of tin(IV) chloride to give 3-acyl-4-amino-2(5H)-furanones (2) and ethyl 4-amino-2,5-dihydro-2-oxofuran-3-carboxylates (3). The acyldihydrofuranones (2) can be converted into acyltetronic acid derivatives (6) while the ethyl furan-3-carboxylates (3) can be converted into tetronic acids (8).