Synthesis of Pharmacologically Important Perimidines using Eco-Friendly Deep Eutectic Solvents

Area of Science:

• Green Chemistry
• Organic Synthesis
• Materials Science

Background:

• Traditional synthesis of perimidine derivatives often involves hazardous solvents and expensive catalysts.
• There is a growing need for sustainable and environmentally benign chemical processes.
• Deep eutectic solvents (DESs) have emerged as promising alternatives for various chemical transformations.

Purpose of the Study:

• To develop a green and efficient protocol for synthesizing diverse perimidine derivatives.
• To utilize deep eutectic solvents (DESs) as both reaction media and catalysts.
• To explore the potential of DESs in producing bioactive molecules and sensors.

Main Methods:

• Synthesis of perimidine derivatives using 1,8-diaminonaphthalene with aldehydes or ketones.
• Employing deep eutectic solvents (DESs), specifically choline chloride (ChCl)/N,N'-dimethylurea (DMU) and DMU/L-(+)-tartaric acid, as reaction media and catalysts.
• Characterization of synthesized compounds using NMR spectroscopy, mass spectrometry, IR spectroscopy, and X-ray diffraction analysis.

Main Results:

• Successful synthesis of various functionalized perimidines in good-to-excellent yields under mild, eco-friendly conditions.
• Identification of optimal DESs (ChCl/DMU for aldehydes, DMU/tartaric acid for ketones).
• Demonstrated scalability and reusability of the DES-mediated method, with preliminary photophysical properties reported.

Conclusions:

• The developed DES-mediated protocol offers a sustainable and efficient route for perimidine synthesis.
• The method avoids hazardous solvents and expensive catalysts, aligning with green chemistry principles.
• The synthesized perimidines, including bioactive molecules and a sensor, show potential for various applications, and the method is suitable for industrial scale-up.