Synthesis of N-substituted Acridinediones and Polyhydroquinoline Derivatives in Refluxing Water

Abstract

Acridinediones were synthesized by the one-pot Hantzsch condensation of an aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedione, and aniline/4-methylaniline in refluxing water. This method has then been extended to the four-component reaction of an aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedione, ethyl acetoacetate and ammonium acetate for the synthesis of polyhydroquinoline derivatives. This is an environmentally friendly and efficient procedure providing good to excellent yields.

A solvent-free synthesis of polyhydroquinolines via Hantzsch multicomponent condensation catalyzed by nanomagnetic-supported sulfonic acid

“…This method has the following advantages: Magnetic separation can eliminate expensive centrifugation (compared to methods using nano catalysts without magnetic properties 22 ), nano-sized magnetic particles have large specific surface area so adsorption capacity is high, for this reason, the reaction rate increased leading to energy savings. In contrast to other methods, [23][24][25][26][27][28][29][30][31][32][33][34] the products are obtained in a shorter time. These results clearly indicate that nano-g-Fe 2 O 3 -SO 3 H is an efficient, magnetic and reusable acidic catalyst, and the present method is found to be very effective for the synthesis of polyhydroquinoline derivatives.…”

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

“…The reaction of aldehydes 1 with dimedone 72 and ammonium acetate or aniline derivatives in the presence of different catalysts and solvents afforded 5 H ‐acridine‐1,8‐dione derivatives 131 (Methods A‐E, Scheme , Table ) …”

Synthesis, Structure, and Biological Activities of 10‐Substituted 3,3,6,6‐Tetramethyl‐9‐Aryl‐3,4, 6,7,9,10‐hexahydroacridine‐1,8(2H,5H)‐dione Derivatives

“…They are widely used as anticancer, antibacterial, DNA probe, antitumor, and so on. Therefore, many studies have been carried out on acridinedione derivatives. Tetraketones are extensively used as important precursors for the synthesis of various acridinediones.…”