A Lewis Acid-Catalyzed Cascade Synthesis of Fused N-Heterocycles from 2-Alkynylanilines and 2-Formylbenzonitriles: Unveiling Iminoisoindoloindolone and Its Derivatives

Abstract

We herein reveal a streamlined synthesis of structurally fused 6-iminoisoindoloindolones via a meticulously orchestrated cascade reaction. This process seamlessly intertwines 2-alkynylaniline and 2-formylbenzonitrile under the catalytic influence of TMSOTf, giving rise to these compounds in remarkable yields that stand as a testament to the efficiency of our approach. Moreover, the versatility of this synthetic strategy extends far beyond mere synthesis, offering a gateway to the creation of both isoindoloindolone and unprecedented diphenylbenzopyrrolizinoisoquinolinone derivatives, thereby opening new horizons in the realm of chemical innovation. Furthermore, the strategic elegance of this synthetic methodology is underscored by its potential for scale-up production and applicability across diverse chemical contexts.