Angewandte Chemie, Год журнала: 2023, Номер 135(21)

Опубликована: Март 18, 2023

Abstract Metal‐polarized aza‐ ortho ‐quinone methides (aza‐ o ‐QMs) are a unique and efficient handle for azaheterocycle synthesis. Despite great achievements, the potential of these reactive intermediates has not yet been fully exploited, especially new reaction modes. Herein, we disclosed an unprecedented dearomatization process metal‐polarized ‐QMs, affording transient dearomatized spiroaziridine intermediates. Based on this serendipity, accomplished three sequential dearomatization‐rearomatization reactions benzimidazolines with aza‐sulfur ylides, enabling divergent synthesis bis‐nitrogen heterocycles high efficiency flexibility. Moreover, experimental theoretical studies were performed to explain proposed mechanisms observed selectivity. Further cellular evaluation dibenzodiazepine products identified hit compound antitumor drugs.

Язык: Английский