Domino Reaction Of Arylaldehydes And 1-acetylcyclopropane Carboxamides

The feature of domino reactions is creation of molecular complexity and diversity from simple substrates in a vessel. Without the separation of intermediates, domino reactions could afford products with higher yield than traditional reactions. Domino reactions allow multiple bonding events and efficient synthesis. However, the development of domino reactions constitutes a great challenge in an enviromentally benign and atom-economic fashion in modern organic chemistry both from academic and industrial points of view.In this paper, we developed a domino reaction based on arylaldehydes and 1-acetylcyclopropanecarboxamides, which allows one-pot and efficient synthesis of structurally complex piperidine-2,4-diones with multiple functionalities under mild conditions. The overall transformation involves tandem aldol/intramolecular aza-Michael/(aldol)/Michael sequences. Moreover, when excessive arylaldehydes were employed, spiropiperidine-2,4-diones 6 would be obtained, which supports the possible mechanism we proposed for the highly efficient one-pot transformation into spiropiperidine-2,4-diones 3.