Reduction of Cyclic Imides. III. Reduction of 3- and 4-Substituted Phthalimides with Sodium Borohydride

概要

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Reduction of 3-substituted phthalimides with sodium borohydride in 90% methanol was found to give one kind each of reduction product and solvolysis product. In the case of an electron-withdrawing nitro group, the carbonyl group in 2-position was selectively reduced to the hydroxyl group, whereas in the case of an electron-donating amino, acetamido, hydroxyl, or methoxyl group, the carbonyl group in 1-position was reduced to the methylene group, and the formation of a solvolysis product increased. In the case of 4-substituted compounds, two kinds each of reduction product and solvolysis product were obtained. When the substituent was a nitro group, ratio of the products from reduction of imidocarbonyl in 1- and 2-position was about 5 : 4,while this ratio became about 4 : 5 inversely in the case of electron-donating substituent groups. In the solvolysis products, the position attacked in the imidocarbonyl and the position reduced became the same, and their ratio was the same as in the reduction products.
公益社団法人日本薬学会の論文
1978-02-25