An efficient synthesis of novel N-acetyl-3-alkanoyl and 3-dienoyl tetramic acids

Abstract

A general synthesis of N-acetyl-3-alkanoyl- and 3-dienoyl-tetramic acids is presented. The condensation of N-(N-acetylglycyloxy)succinimide with β-keto esters bearing alkanoyl or dienoyl groups furnishes the new 3-substituted N-acetyltetramic acids 6–9 and 16 in good yields. The key intermediates 4 and 5 have been isolated and subsequently cyclized to the corresponding tetramic acids. Spectral data for and the physical characteristics of all compounds are reported.