Hantzsch one-pot multicomponent synthesis of a novel series of bis(9,10-diarylhexahydroacridine-1,8-diones)

Abstract

Efficient procedures have been developed for the synthesis of novel series of bis(9,10-diaryl-hexahydroacridine-1,8-diones) in which the two acridine moieties were linked to aliphatic, aromatic, or heteroaromatic spacers via ether or ester linkages. The target products were obtained in good to excellent yields via a multi-component reaction of the appropriate aromatic amine, 5,5-dimethyl-1,3-cyclohexanedione, and the corresponding bis-aldehydes. The reactions were also proceeded to give the target products in good yields via a multi-component reaction of the appropriate cyclic enamines, and the corresponding bis-aldehydes under similar conditions. Bis-alkylation of the appropriate hexahydroacridine-1,8-dione with the corresponding dihalo compound in a basic medium was also proved to be an effective strategy for the synthesis of the target products. The multi-component reaction of the aromatic amine, bis-aldehydes, and barbituric acid or 1,3-dimethylbarbituric acid, instead of 5,5-dimethyl-1,3-cyclohexanedione, afforded the corresponding Knoevenagel condensation adducts in good yield and unfortunately, the expected bis-tetrahydropyrimido[4,5-b]quinolines could not be isolated.

Graphical Abstract

Keywords:

• Bis(aldehydes)
• 5,5-dimethylcyclohexane-1,3-dione
• multi-component reaction
• enaminones
• bis(9,10-diarylhexahydroacridines)