Utilizing an Old Idea for the Three-Component Synthesis of Anthraquinone-Scaffold-Based Enaminodiones (2,2-Diacylethenamines)

Abstract

An efficient, novel, and direct approach synthetic protocol for the construction of anthraquinone scaffold-based aminomethylene cycloalkane-1,3-diones (enaminodiones) is described. The developed one‐pot scheme involves amino-methylene bond formation to access the desired product. The green synthetic procedure has been accomplished by reacting to a wide variety of 1,3-dicarbonyl compounds, amino anthraquinones, and triethyl orthoformate in acetic acid at room temperature in good yields. Their chemical structures building blocks containing enaminodiones-anthraquinone framework were identified by melting points, ¹H NMR, ¹³C NMR, elementary analysis, Fourier transform-infrared, and mass spectra. Furthermore, the DNA binding activities of these compounds were investigated by electronic absorption spectra UV–vis.

Graphical Abstract

Keywords:

• Acetic acid
• amino anthraquinone
• 1,3-dicarbonyl compounds
• enaminodiones-anthraquinone framework
• triethyl orthoformate

Additional information

Funding

We wish to express our thanks to the Research Council of the University of Sistan and Baluchestan for the financial support of this work.