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Updated: Oct 23, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
EDA complex-enabled, substituent-controlled switch in anthranil reactivity for sequential access to azaaurones
Khushboo Tiwari1,2, Mayank Singh1,2, Annapurna Awasthi1,2
1Department of Biological and Synthetic Chemistry, Center of Biomedical Research (CBMR), SGPGIMS Campus, Raibareli Road, Lucknow, U.P, 226014, India. dkt80.org@gmail.com.
Abstract:
A sequential protocol has been developed for the synthesis of azaaurones from readily available anthranils and olefins. The transformation proceeds via palladium-catalyzed C3-alkenylation of anthranils to afford C3-styrylanthranil intermediates, which subsequently undergo skeletal rearrangement in the presence of THIQ·HCl. Mechanistic studies suggest that THIQ·HCl forms an electron donor-acceptor (EDA) complex with the styrylanthranil intermediate, facilitating N-O bond cleavage and nitrene generation. The resulting nitrene undergoes cyclization to form an aziridine intermediate, which subsequently rearranges to afford the azaaurone. Notably, the compatibility of this protocol with biologically relevant styrene derivatives highlights its potential for the late-stage functionalization of complex molecules.
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