Acylanthranils. 11. Reaction of acylanthranils with alcohols to give the corresponding esters

…, PE Ashley, JJ McBrady, DR Yarian

Index: Errede, L.A.; Ashley, P.E.; McBrady, J.J.; Yarian, D.R. Journal of Organic Chemistry, 1982 , vol. 47, # 20 p. 3825 - 3828

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Citation Number: 10

Abstract

Although the reactions of acetylanthranil (1, R= CHJ with nucleophilic molecules of the type HNu usually occur “abnormally” via nucleophilic attack at the less electropositive center, C-2 (pathway A, Scheme 11), it was shown that reactions of 1 with the anion form, Nu-, always occur “normally” via nucleophilic attack at the more electropositive center, C-4 (pathway B, Scheme 11). Thus, reaction of 1 with ROH in the presence of a small amount of RO-gives ...