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СпутникиРНSpaceXРоскосмосNASAAbstractThis article presents an alternative method for synthesizing flavones from chalcones using copper(I) iodide (CuI) and two azides-sodium azide and 4‑azidobenzenesulfonamide-as key reagents. The azides most likely undergo a Michael addition with chalcones to form 1,2,3‑triazoles, mediated by either stoichiometric or catalytic amounts of CuI. Interestingly, the expected 1,2,3‑triazoles were not obtained; instead, the forming 1,2,3‑triazoles intermediates appeared to undergo immediate intramolecular attack by the C2 hydroxy group of the A‑ring of chalcones, followed by elimination of the azides, ultimately yielding flavones. The yields and reaction rates were influenced by the varying amounts of CuI and azides employed. The key role of azides was not only to act as nucleophiles and leaving groups, but also to accelerate the reaction rate in the presence of CuI, in contrast to reactions conducted with CuI alone as previously reported. The unique mechanistic pathway was examined in detail.This document is a preprint and has not been non-peer-reviewed.Beilstein Arch. 2026, 202628. doi: 10.3762/bxiv.2026.28.v1
This article presents an alternative method for synthesizing flavones from chalcones using copper(I) iodide (CuI) and two azides-sodium azide and 4‑azidobenzenesulfonamide-as key reagents. The azides most likely undergo a Michael addition with chalcones to form 1,2,3‑triazoles, mediated by either stoichiometric or catalytic amounts of CuI. Interestingly, the expected 1,2,3‑triazoles were not obtained; instead, the forming 1,2,3‑triazoles intermediates appeared to undergo immediate intramolecular attack by the C2 hydroxy group of the A‑ring of chalcones, followed by elimination of the azides, ultimately yielding flavones. The yields and reaction rates were influenced by the varying amounts of CuI and azides employed. The key role of azides was not only to act as nucleophiles and leaving groups, but also to accelerate the reaction rate in the presence of CuI, in contrast to reactions conducted with CuI alone as previously reported. The unique mechanistic pathway was examined in detail.
Keywords: azide; chalcone; copper iodide; flavone
When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:
Chen, S.-X.; Su, Y.-J.; Wu, H.-Y.; Cheng, S.-C.; Shih, T.-L. Beilstein Arch. 2026, 202628. doi:10.3762/bxiv.2026.28.v1
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© 2026 Chen et al.; licensee Beilstein-Institut.
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