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Zenichi Yoshida (1925-2023)
Zenichi Yoshida (1925-2023)
Professor. Zenichi Yoshida,
a member of the Honorary Advisors of HETEROCYCLES (1975-1998),
has passed away on May 4, 2023 at the age of 97.
I deeply express my regret over his death.
Kunio Ogasawara
Editor
May 11, 2023
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Paper | Special issue | Vol 40, No. 1, 1995, pp.285-292
Published online, 1st January, 1970■ Synthesis of Isoxazoles Bearing Methoxycarbonyl and Formyl Groups by 1,3-Dipolar Cycloaddition of Nitrile Oxides to Olefinic and Acetylenic Dipolarophiles
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
Abstract
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.
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