Base-Induced Alcoholysis of N-Arylmaleimides: Facile in situ Oxa-Michael Addition to Alkyl Maleanilates: Two-Step One-Pot Rapid Access to Alkoxysuccinic Acids [1]

Abstract

A simple, efficient and general two-step, one-pot approach to alkoxysuccinic acids is described. The potassium carbonate-catalyzed reactions of alcohols with N-p-tolylmaleimide (4) followed by an acid-induced hydrolysis of intermediate products furnished alkoxysuccinic acids 1a-f in 90-98% yields. All the intermediates from the reaction of imide 4 with alcohols have been isolated and characterized, proving that the in situ formed alkyl maleanilates 3 are the actual Michael acceptors.

Key words

N-arylmaleimides - alkyl maleanilates - oxa-Michael addition - alkoxysuccinic acids

1

NCL Communication No. 6630.

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NCL Communication No. 6630.

23

The (±)-methoxysuccinic acid(1a) has also been obtained in small amounts by chemical degradation of α-methylvanillyl alcohol [24a] and methylated sugars. [24b]