# Greener Synthesis of 4‑Selanyl-Isocoumarins Mediated by TCCA: Electrochemical Insights and DNA Interaction Studies

## TL;DR

A new eco-friendly method for making 4-selanyl-isocoumarins is developed, with potential applications in DNA-targeted drug design.

## Contribution

A sustainable, metal-free synthesis of 4-selanyl-isocoumarins using TCCA is introduced, with insights into electrochemistry and DNA interactions.

## Key findings

- 4-selanyl-isocoumarins are synthesized efficiently using TCCA under ambient conditions with up to 98% yield.
- Electrochemical and DFT studies confirm the redox activity and structural stability of the compounds.
- DNA binding studies show dual interaction modes, suggesting potential in DNA-targeted drug development.

## 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.