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Updated: Nov 30, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Access to Polycyclic Azepino[5,4,3-cd]indoles via a Gold-Catalyzed Post-Ugi Dearomatization Cascade
Yi He1, Liangliang Song1, Chao Liu1
1Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.
Abstract:
The development of a rapid and diverse access to complex natural product-like 3,4-fused indole scaffolds has always attracted considerable attention from synthetic and medicinal communities. We herein disclose a modular and straightforward protocol to prepare the densely substituted polycyclic azepino[5,4,3-cd]indole scaffolds. This synthetic process involves an Ugi four-component reaction from easily available starting materials and a gold-catalyzed post-Ugi domino dearomatization/Michael addition sequence, enabling facile access to the highly functionalized azepino[5,4,3-cd]indole core with excellent chemo-, regio-, and diastereoselectivity.
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