ArticleACS omega2025
Greener Synthesis of 4‑Selanyl-Isocoumarins Mediated by TCCA: Electrochemical Insights and DNA Interaction Studies.
Article in ACS omega, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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8 authors.
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Abstract
We present a straightforward and sustainable approach for the synthesis of 4-selanyl-isocoumarins from 2-(alkynyl)-aryl or -heteroaryl and diorganoyl diselenides. This transformation employs trichloroisocyanuric acid (TCCA) as a low-cost, metal-free oxidant under ambient conditions, delivering the desired products in yields of up to 98%. Mechanistic investigations support an electrophilic activation of the alkyne followed by a 6-endo-dig cyclization. Electrochemical and DFT analyses confirm the redox activity and structural stability of the resulting compounds. Additionally, DNA binding studies, combining UV-vis spectroscopy and molecular docking, reveal dual interaction modes (intercalation and groove binding), underscoring their potential in DNA-targeted drug design.
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