Tandem Reactions of 1,3-Diacid Chlorides with 2-Methylimidazoline and 2-Methyl-1,4,5,6-tetrahydropyrimidine: One-Pot Synthesis of 1,8-Naphthyridinetetraones

Abstract

The reactions of 2-methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine with 1,3-diacid chlorides, in the presence of Et3N in refluxing MeCN give highly functionalized potentially bioactive 1,8-naphthyridinetetraones. 2-Methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine can be viewed as tridentate nucleophiles which give four consecutive tandem nucleophilic attacks on electrophiles.