Construction of a spiro[pyrazolone-4,2′-pyridoindole] scaffold via a [3 + 3] cycloaddition of 2-indolylmethanol with a 4-aminopyrazolone-derived azomethine ylide

Abstract

This work reports a facile [3 + 3] cycloaddition sequence of two important heterocyclic pharmacophores, pyrazolone and 2-indolylmethanol, integrated into a polycyclic hybrid scaffold. In this process, an in situ generated azomethine ylide obtained from 4-aminopyrazolone and benzaldehyde reacts with 2-indolylmethanols to offer spiro[pyrazolone–pyridoindole] scaffolds in high yields with excellent diastereoselectivities. Remarkably, the reaction is carried out at room temperature without any catalyst and base.