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Paper | Regular issue | Vol 38, No. 6, 1994, pp.1307-1316
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6679
Cycloaddition of Nitrile Oxides to 4-Oxobut-2-enoic Acid Derivatives

Francisco Fariña, M. Rosario Martín,* M. Victoria Martín, and Ana Martínez de Guereñu

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain


The 1,3-dipolar cycloadditions of aceto-, benzo- and bromoformonitrile oxides to cyclic and open-chain 4-oxobut-2-enoic acid derivatives have been investigated. The addition to 5-methoxyfuran-2(5H)-one (1) gave regioselectively 3-substituted 6-exo-methoxy-3a,6a-dihydrofuro[3,4-d]isoxazol-4(6H)-ones, whereas methyl (Z)- and (E)-4,4-dimethoxybut-2-enoates (2) and (3) afforded mixtures of regioisomeric isoxazolines.