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Paper | Special issue | Vol 40, No. 1, 1995, pp.285-292
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S27
Synthesis of Isoxazoles Bearing Methoxycarbonyl and Formyl Groups by 1,3-Dipolar Cycloaddition of Nitrile Oxides to Olefinic and Acetylenic Dipolarophiles

Francisco Fariña, M. Teresa Fraile, M. Rosario Martin, M. Victoria Martín, and Ana Martínez Guereñu

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


The 1,3-dipolar cycloadditions of benzo-, bromoformo- and acetonitrile oxides to enamino ester (1) and acetylenic esters (2, 3) afforded functionalized isoxazoles in moderate to good yields. Cycloadditions with the enamino ester (1) gave the corresponding methyl 5-dimethoxymethylisoxazole-4-carboxylate (7a-9a) as the sole regioisomer, whereas the reactions with acetylenic dipolarophiles (2, 3) were generally less selective and the regioselectivity depended significantly on the nature of the substituents of the dipole and the acetylenic ester.