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Chromone-Thiocoumarin Transmutation Enabled by Lawesson's Reagent.

Yu-Chen Fang1,2,3, Li-Ping Tu1, Hui-Min Li1,3

  • 1Guizhou Provincial Key Laboratory of Innovation and Manufacturing for Pharmaceuticals, School of Pharmacy, Zunyi Medical University, Zunyi 563006, P. R. China.

Organic Letters
|January 27, 2026
PubMed
Summary

Medicinal chemists can now efficiently convert chromone molecules into thiocoumarins, which are valuable biologically active compounds. This skeletal transmutation using Lawesson's reagent offers a new pathway for drug discovery and development.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Selective modification of molecular skeletons is crucial for discovering new drug leads.
  • Chromone derivatives are common starting materials, but their transformation into other biologically relevant scaffolds can be challenging.

Purpose of the Study:

  • To develop an efficient protocol for the skeletal transmutation of chromone derivatives into thiocoumarins.
  • To explore the synthetic utility of this transformation in medicinal chemistry.

Main Methods:

  • Chromone derivatives were reacted with Lawesson's reagent under heating in toluene.
  • The reaction proceeds via a cascade of ring opening, rearrangement, and cyclization.
  • Mechanistic studies utilized 18O-labeled substrates to trace atom origins.

Main Results:

  • A series of thiocoumarins were successfully synthesized from chromone precursors.
  • The protocol demonstrated synthetic utility through gram-scale synthesis and late-stage modification of estrone.
  • Mechanistic studies confirmed the origin of the silicon-bound oxygen atom.

Conclusions:

  • This study presents an efficient method for converting chromones to thiocoumarins, a biologically privileged scaffold.
  • The developed skeletal remodeling strategy is valuable for lead compound discovery and modification in medicinal chemistry.