183737-75-9

Upstream product

• 889-31-6 5,5-dimethyl-3-benzylamino-2-cyclohexen-1-one 
• 100-52-7 benzaldehyde 
• 126-81-8 dimedone 
• 100-46-9 benzylamine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 2769-21-3 3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione 

Relevant academic research and scientific papers

Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction

A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic and kinetic study, some controlled experiments and deuterium labeling experiments were executed. A time-dependent product distribution experiment is also presented and the reaction scale-up is performed to highlight the practical utility of this strategy.

An efficient route to 1,8-dioxo-octahydroxanthenes and -decahydroacridines using a sulfated zirconia catalyst

Sulfated zirconia results to be a very efficient catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines without tedious work-up procedures. While 1,8-dioxo-octahydroxanthenes are prepared from aldehyde and 5,5-dimethyl-1,3-cyclohexenedione (dimedone), 1,8-dioxo-decahydroacridines are prepared from this reactant mixture with amines. This method provides a mild catalytic protocol for the synthesis of functionalized xanthene and acridine derivatives. The catalysts were characterized by XRD, FT-IR, TGA-DSC, SEM-EDAX and surface acidity and showed excellent re-usability up to 6 consecutive cycles.

Cross-dehydrogenative regioselective Csp3-Csp2 coupling of enamino-ketones followed by rearrangement: An amazing formation route to acridine-1,8-dione derivatives

A new general method for the synthesis of acridine-1,8-diones through CDC coupling of enamino-ketones followed by rearrangement has been developed. This is a Cu(i) catalyzed procedure, based on the cross dehydrogenative coupling of the Csp3-H b

Competitive one-pot reactions: Simultaneous synthesis of decahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes and photophysical characterization

A simple and convenient one-pot method for simultaneously obtaining decahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthene derivatives is described. A high conversion yielding both products was obtained under the reaction conditions. To understand the optical behavior of the model compounds and their potential use as antenna moieties in bichromophoric systems, the photophysical properties of all samples were studied using ultraviolet-visible absorption and steady-state fluorescence spectroscopy in methanol solutions. For the case of the acridinediones, the fluorescence spectra were found to exhibit the typical emission profile of the locally excited state, whereas, contrary to previous published experimental results, reliable fluorescence emission spectra for the xanthenes derivatives could not be obtained. On the other hand, the poor quantum yields of the synthesized decahydroacridine-1,8-diones were explained based on the benzene-like substitution effect, which favors the intersystem crossing relaxation mechanism. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright

Magnetically recoverable, nanoscale-supported heteropoly acid catalyst for green synthesis of biologically active compounds in water

12-Tungstophosphoric acid supported on aerosil silica and silica-coated γ-Fe2O3 nanoparticles was prepared and characterized using transmission electron microscopy, scanning electron microscopy, and inductively coupled plasma atomic emission spectroscopy. The catalytic activity of the two prepared catalysts was compared in the synthesis of 1,8-dioxo-9,10- diaryldecahydroacridines in water. 12-Tungstophosphoric acid was highly dispersed on the silica-coated γ-Fe2O3 nanoparticles and showed higher activity and a higher reuse number compared with the acid supported on aerosil silica. The catalyst could be recovered simply by using an external magnetic field and could be reused several times without appreciable loss of its catalytic activity.

Efficient one-pot synthesis of acridinediones by indium(III) triflate-catalyzed reactions of β-enaminones, aldehydes, and cyclic 1,3-dicarbonyls

An efficient one-pot synthesis of acridinediones by In(OTf) 3-catalyzed reactions was developed starting from β-enaminones, aldehydes, and cyclic 1,3-diketones. The key strategies of these reactions involve domino Knoevenagel condensation/Michael addition/cyclodehydration reaction.

Ceric ammonium nitrate (CAN) catalyzed synthesis of N-substituted decahydroacridine-1,8-diones in PEG

Polyethylene glycol (PEG) was found to be an inexpensive non-toxic and effective medium for the one-pot synthesis of N-substituted decahydroacridine-1,8-diones in the presence of ceric ammonium nitrate (CAN) as the catalyst in high yields. Also, the solve

Synthesis of 9-R1-10-R-1,8-dioxo-decahydroacridines and dioximes based on them

3,3,6,6-Tetramethyl-9-R1-10-R-1,8- dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridines were synthesized through the intermediate α-R-methylenebisenamino ketones by the condensation of 5,5-dimethyl-3-N-R-aminocyclohex-2-enones with aliphatic, aromatic, and furan aldehydes (2-propanol, phosphorus pentoxide). It was found that the degree of substitution of the heterocycle in decahydroacridinediones has an effect on the direction of their transformations during oximation.

One pot facile synthesis of some new 9,10-dihydroacridine derivatives

A convenient one pot synthesis of 9,10-dihydroacridine derivatives 3a-f and 4a-d has been described by the condensation of N-methylaniline or 5,5-dimethyl-3-benzylamino-2-cyclohexen-1-one with appropriate aromatic adehydes (1) and 5,5-dimethylcyclohexane-1, 3-dione (2) in methanol. These final products can alternatively be obtained from bis-dimedonyl derivatives (5) and 2-arylidene-5,5-dimethylcyclohexane-1,3-dione (6) on reaction with N-methylaniline or 5,5-dimethyl-3-benzylamino-2-cyclohexen-1-one and suggest the key steps to reaction mechanism.