11H-isoindolo[2,1 -a]indol-11-ones: novel rearrangement products from the attempted preparation of 2-(2-diethylaminomethylphenyl)isatogens

Abstract

The attempted synthesis of 2-(2-diethylaminomethylphenyl)isatogens, from appropriately substituted phenylacetylenes and aromatic iodo compounds by two different routes gave novel substituted 11H-isoindolo[2,1 -a]indol-11-ones (6a–d) as the only identifiable products. Their structures were established from spectroscopic and chemical studies. A mechanism, involving the rearrangement of the expected isatogens to isoindoloindoles, is proposed.