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Natural products containing nitrogen in heterocycles are the central attraction of various drug candidates. Furthermore, the presence of an acridine and 1,4-naphthoquinone moiety in these congeners considerably enhanced their biological activities. Therefore, there is an urgent need to develop an efficient method for 7-arylbenzo[c]acridine-5,6(7H,12H)-dione synthesis.
To synthesize 7-arylbenzo[c]acridine-5,6(7H,12H)-dione, 2-hydroxy-1,4-naphthoquinone, aromatic aldehydes, and aromatic amines were mixed in a single reaction vessel at room temperature without special precautions. To this mixture, nicotinic acid was employed as a catalyst in ethanol as the solvent.
24 different 7-arylbenzo[c]acridine-5,6(7H,12H)-dione derivatives have been synthesized successfully with good yields.
This metal-free annulation strategy provides several significant advantages, including simplicity of reaction operation, shorter reaction time, use of affordable starting materials, and simple product purification techniques. These nonaromatic acridine derivatives can be conveniently transformed into their aromatic derivatives, which represents a novel finding of this approach.
A one-pot annulation approach to assemble 7-arylbenzo[c]acridine-5,6(7H,12H)-dione derivatives has been developed via cascade condensation of 2-hydroxy-1,4-naphthoquinone, aromatic aldehydes, and aromatic amines, with the first-time use of nicotinic acid as a catalyst. The potential reusability of nicotinic acid further enhances the method's attractiveness compared to existing approaches.
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