Synthesis of spiroindolenine–cyclopentenedione skeletons and their chemical behaviours: the first example of a lactone-type spiroindolenine structure

Abstract

A manageable, one-pot, and high-yield protocol for synthesising highly reactive spiroindolenine derivatives is reported. Spiroindolenines are furnished by a reaction between DCC (dicyclohexylcarbodiimide) and indole-3-butenoic acid derivatives. The protocol proposed here involves the construction of a carbon–carbon bond through intramolecular domino cyclisation. The reaction mechanism for spirocyclisation is discussed; both NMR and X-ray analysis were used to verify the structure of spiroindolenine. The applied strategy allowed the formation of spiroindolenine with a dione substructure, which is an unknown compound with a spirocyclic nucleus. Further reactions of spiroindolenines with di-amines, a primary amine, and alcohol have been reported, and new types of indole derivatives, such as indoloquinoxalines, where the spirocentre atom undergoes a nucleophilic attack, are yielded.