Highly efficient neat synthesis of xanthenediones and acridinediones

Abstract

In the absence of any solvent, the reactions of various aromatic aldehydes with 5,5-dimethyl-1,3-cyclohexanedione catalyzed by methanesulfonic acid under thermal heating conditions smoothly afforded 9-aryl-3,3,6,6-tetramethyl-tetrahydroxanthene-1,8-diones in nearly quantitative yields. Under the same melting conditions, rapid and efficient synthesis of 9-aryl-3,3,6,6-tetramethylhexahydroacridine-1,8-diones and 9,10-diaryl-3,3,6,6-tetramethyl-hexahydroacridine-1,8-diones could also be achieved using ammonium acetate and p-toluidine as the nitrogen source.

Recent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesis

“…Shen and co-workers 253 have reported the synthesis of 9-aryl-3,3,6,6-tetramethyl-tetrahydroxanthene-1,8-diones 327 in nearly quantitative yields by the coupling of various aromatic aldehydes 326 and 5,5-dimethyl-1,3-cyclohexanedione 166 catalyzed by methanesulfonic acid under solvent-free conditions (Scheme 94).…”

Multicomponent Reactions Promoted by Ecocatalyst from Metal Hyperaccumulating Plant Pluchea sagittalis

“…3,3,6,6-Tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (5a) [35]: light yellow solid (0.171 g, 98%); m.p. 276-278 • C. 1 (4-Chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (5b) [35]: light yellow solid (0.180 g, 94%); m.p.…”

“…3,3,6,6-Tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (5a) [35]: light yellow solid (0.171 g, 98%); m.p. 276-278 • C. 1 (4-Chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (5b) [35]: light yellow solid (0.180 g, 94%); m.p. 296-298 • C. 1 4-(3,3,6,6-Tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahy-droacridin-9-yl) benzonitrile (5c) [36]: light yellow solid (0.148 g, 79%); m.p.…”

Acridine‐1,8‐diones: Synthesis and Biological Applications

“…In 2006, Wang and Miao [171] developed a one-pot Hantzsch synthesis from easily available substrates, substituted benzaldehydes, enaminones and dimedone under aqueous and solventfree conditions to furnish 4-arylacridinedione derivatives with high efficiency without using any organic reagents and catalyst [Scheme 25, Method 1]. Afterwards, Shen and Wang [172] reported an environment-friendly solvent-free and catalyst-free synthesis of 9,10-substituted-3,3,6,6-tetramethylhexahydroacridine-1,8-diones in excellent yields without using long purification process [Scheme 25, Method 2] Bhuva and Patel [173] synthesized substituted acridinediones and evaluated their bio-potency against microbes and tuberculosis. The regioselective reaction of dimedone, 7-substituted tetrazolo [1,5-a]quinoline-4-carbaldehyde, and 3,4-substituted phenylamino)-5,5-disubstituted cyclohex-2-enones (5) in acetic acid yielded a range of tetrazolo [1,5-a] The anti-inflammatory and anti-diabetic activity of acridinediones were scrutinized by Mallu and companions.…”