Functionalized 4-hydroxy coumarins: novel synthesis, crystal structure and DFT calculations

Area of Science:

• Organic Chemistry
• Medicinal Chemistry

Background:

• Coumarins are important heterocyclic compounds with diverse biological activities.
• Efficient synthesis of functionalized coumarins remains a key challenge in organic chemistry.

Purpose of the Study:

• To develop a novel, short-step methodology for synthesizing functionalized coumarins.
• To explore a tandem C-acylation-cyclization process for coumarin synthesis.

Main Methods:

• Synthesis initiated from the N-hydroxysuccinimide ester of O-acetylsalicylic acid.
• Employed a tandem C-acylation-cyclization reaction sequence.
• Utilized X-ray diffraction and Density Functional Theory (DFT) calculations for structural analysis.

Main Results:

• Achieved good yields of functionalized coumarins.
• Established the structure of 3-methoxycarbonyl-4-hydroxy coumarin via X-ray diffraction.
• Validated geometric parameters using DFT calculations.

Conclusions:

• The developed methodology provides an efficient route to functionalized coumarins.
• The tandem C-acylation-cyclization is effective under mild conditions.
• Structural and computational analysis confirmed the synthesized coumarin derivative.