Studies on pyrrolidinones. synthesis of fused 1,5-naphthyridines

The synthesis of new condensed indolizinediones derived from pyroglutamic acid is described. The Semmler–Wolff transposition of the oxime of these ketones leads to fused dihydro-1,5-naphthyridinones. Easy introduction of side amino chains indicates that potential DNA-intercalating heterocyclic systems fused on 1,5-naphthyridine nucleus could be obtained in these series.

Graphical abstractThe synthesis of new condensed indolizinediones derived from pyroglutamic acid is described. The Semmler–Wolff transposition of the oxime of these ketones leads to fused dihydro-1,5-naphthyridinones. Easy introduction of side amino chains indicates that potential DNA-intercalating heterocyclic systems fused on 1,5-naphthyridine nucleus could be obtained in these series.Figure optionsDownload full-size imageDownload as PowerPoint slide