Synthesis of Dihydro‐benzazepinoindoles via an Oxidative Pictet–Spengler Reaction

Abstract Benzazepinoindoles represent a fascinating class of heterocyclic compounds known for their structural complexity and significant biological activity including potential anticancer and antimicrobial activities. The benzazepinoindole scaffold, notable for its biological relevance serves as an ideal template for drug discovery particularly for applications in antiproliferative, anti‐inflammatory, and anticancer therapies. In this work, we have developed an efficient methodology for the synthesis of dihydro‐ and tetrahydro‐benzazepinoindoles catalysed by cyanuric chloride (TCT). This approach is strategically designed to enable the synthesis of both dihydro and tetrahydro derivatives with minimal modifications to the reaction conditions. This methodology employs a strategic approach, ensuring moderate to good yields, and through this process, we aimed to synthesize a wide range of benzazepinoindole derivatives, incorporating various functional groups to enhance their structural diversity. The scalability of this method was demonstrated through successful gram‐scale syntheses, validating its practical applicability. Characterization of the synthesized compounds was carried out using various techniques, including 1 H NMR, 13 C NMR, DEPT‐135, and Mass spectrometry confirming the structural integrity and purity of the products. Our work provides an efficient and reliable strategy for constructing complex benzazepinoindole structures, advancing both the field of synthetic chemistry and the development of novel bioactive molecules with enhanced therapeutic potential.