Technology reports of the Yamaguchi University

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Technology reports of the Yamaguchi University Volume 4 Issue 1
published_at 1987-12

1, 3-dipolar addition of nitrile oxides to 3a, 4-dihydro-1-isoindolinones

1, 3-dipolar addition of nitrile oxides to 3a, 4-dihydro-1-isoindolinones
Kakimoto Shinji
Kajigaeshi Shoji
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KJ00004351094.pdf
Descriptions
1,3-Dipolar addition of acetonitrile oxide to 2-phenyl-3a,4-dihydro-1-isoindolinone was carried out in a stereoselective but regiorandam manner. However, the introduction of substituent, e. g., methyl group, at the 4-position of the 1H-isoindol-1-one system turned out to improve regioselectivity of the addition. The regio- and stereoselective isoxazoline synthesis was also accomplished in the reaction with other nitrile oxides. The transformation of the isoxazoline ring was also examined.