Ultrasound-promoted one-pot four-component synthesis of novel biologically active 3-aryl-2,4-dithioxo-1,3,5-triazepane-6,7-dione and their toxicity investigation

Abstract

We have described a novel four-component reaction (4MCR) between oxalyl chloride 1, anilines 2a–h, and two molecules of ammonium thiocyanate 3 in acetone under ultrasound irradiation to give 3-aryl-2,4-dithioxo-1,3,5-triazepane-6,7-diones. A synthetically useful ultrasound effect was observed and title products were obtained in high yields after 15–35 min sonication. Our procedure compared to the conventional heating method has the benefit of higher reaction yields and shorter reaction times. The IR spectra showed the presence of N–H, C═O and C═S groups in these compounds and ¹H, ¹³C NMR and Mass spectral results verified their structures. Cellular investigations showed that these compounds are toxic toward cancer cells.

GRAPHICAL ABSTRACT

KEYWORDS:

• 1
• 3
• 5-triazepane
• oxalyl chloride
• ammonium thiocyanate
• ultrasound irradiation
• toxic

Acknowledgements

The authors appreciate the valuable and helpful comments of Professor Edward L. Clennan, The Editor of Journal of Sulfur Chemistry.

Funding

The partial support of this research by the Research Committee of University of Guilan and Tonekabon Branch, Islamic Azad University is gratefully acknowledged.