36646-78-3

Upstream product

• 873-95-0 1-amino-5,5-dimethylcyclohexen-3-one 
• 106-38-7 para-bromotoluene 
• 106-49-0 p-toluidine 
• 126-81-8 dimedone 

Downstream Products

• 90974-42-8 5,5-dimethyl-cyclohexane-1,3-dione disemicarbazone 
• 65695-53-6 5,5-dimethyl-3-p-toluidino-cyclohex-2-en-one-p-tolylimine 
• 128134-19-0 methyl 5,5-dimethyl-1-oxo-3-(p-toluidino)-2-cyclohexene-2-dithiocarboxylate 
• 311323-36-1 2-amino-4-(4-bromophenyl)-7,7-dimethyl-1-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 
• 339339-19-4 2-amino-7,7-dimethyl-1-(4-methylphenyl)-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 

Relevant academic research and scientific papers

Metal-free syntheses of new azocinesviaaddition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols

A one-pot, clean and green procedure is described for the syntheses of new azocine derivativesviaaddition reactions of enaminones with acenaphthoquinone followed by periodic acid-mediated oxidative cleavages of the corresponding vicinal diols. Various derivatives of azocine were prepared and well characterized. The excellent yields, simple synthesis procedure, lack of a need to carry out any tedious work-up and column chromatography, metal-free catalysis, and mild reaction conditions are important features of this protocol.

A novel and reusable magnetic nanocatalyst developed based on graphene oxide incorporated strontium nanoparticles for the facial synthesis of β-enamino ketones under solvent-free conditions

A novel magnetic SrFeGO nanocatalyst (NC) was synthesized through a simple sol–gel technique by introducing strontium and iron oxide nanoparticles onto graphene. The synthesized NC was characterized using FT-IR and FE-SEM. Subsequently, the catalytic activity of SrFeGO was tested in a reaction between β-dicarbonyl compounds and aniline derivatives to gain β-enamino ketone derivatives under solvent-free conditions. It was found that SrFeGO NC is a potential catalyst for the synthesis of β-enamino ketones. The β-enamino ketone produced by such reactions could be isolated in high purity without the need for chromatographic purifications. The newly prepared magnetic graphene oxide nanocomposite could be recovered and reused for numerous times with no significant decrease in efficiency. Moreover, the protocol has the advantages of excellent yielding (up to 98%) in short a reaction time, benefitting an easy workup procedure and being environmentally friendly.

Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis

A highly efficient and flexible protocol for intramolecular annulation of exocyclic β-enaminones has been disclosed for the synthesis of carbazolones and imidazo[1,2-a]pyridines through a counter-anion-controlled free-radical mechanism promoted by hypervalent iodine(III). The cooperative behavior of HTIB and AgSbF6 plays a crucial role in the intramolecular annulation process through C?C and C?N bond formation to give the desired products. The mechanistic insights suggest that the two competitive reactions involved in the system are guided by the nature of the counteranion, which determines the formation of the final products. A wide variety of carbazolones and imidazo[1,2-a]pyridine molecules have been prepared and isolated in good to excellent yields.

β-Enaminones over recyclable nano-CoFe2O4: a highly efficient solvent-free green protocol

Abstract: β-Enaminone and its derivatives have emerged among the finest bioactive intermediates. High yields of several β-enaminones (86–97%) are achieved through treatment of substituted aromatic and aliphatic amines with cyclic/acyclic 1,3-diketones, over the magnetically separable cobalt ferrite nanoparticles (CoFe2O4 NPs). The latter was prepared upon co-precipitation. Its purity, fine crystallinity, elemental distributions, morphology, magnetic features, and thermal stability were confirmed by Fourier transform infrared, X-ray diffraction, energy dispersive X-ray spectrometry, scanning electron microscopy, vibrating sample magnetometry, and thermal gravimetric analysis analyses. Thus, CoFe2O4 NPs acted as an excellent green heterogeneous nanocatalyst for synthesis of β-enaminones and gave good recyclability, while showing insignificant loss of their activity. Graphical Abstract: [Figure not available: see fulltext.].

Iodine(III)-Promoted Ring Contractive Cyanation of Exocyclic β-Enaminones for the Synthesis of Cyanocyclopentanones

A highly efficient hypervalent iodine-promoted regiocontrolled ring contractive cyanation (RCC) reaction of exocyclic β-enaminones for the synthesis of cyanocyclopentanone (CCP) was demonstrated at ambient temperature with a wide substrate scope. The meth

Nano-SiO2 catalyzed synthesis of β-enaminones under solvent free conditions

Nano-SiO2 efficiently catalyzed the synthesis of β-enaminones using direct condensation of various (cyclic and acyclic) β-diketones with aromatic and aliphatic amines under solvent-free conditions. This eco-friendly catalyst can be recovered and reused without significant loss of activity. This methodology provides a simple synthetic route to enaminones in excellent yields at room temperature. Graphical abstract: [Figure not available: see fulltext.]

Application of dimedone enamines as dienophiles: stereoselective synthesis of amino enols of fused uracils containing a sugar moiety by hetero-Diels-Alder reactions of barbituric acid 5-ylidene alditols with dimedone enamines

Dimedone enamines were applied for the first time as new dienophiles in hetero-Diels-Alder reactions with inverse electron demand. Cycloadditions of barbituric acid 5-ylidene alditols with dimedone enamines were performed in dichloromethane at room temperature for 3 days and fused uracils-chromeno[2,3-d]pyrimidine-2,4-diones were obtained in good 73-87% yields. Only one enantiomerically pure stereoisomer was obtained in each studied cycloaddition. Analysis of 1H NMR and 2D NMR spectra allowed for the determination that cycloadducts exist in solution as mixture of the neutral form and dipolar ion. The prepared fused uracils contain both amine and enol functional groups, so share amphiprotic properties and they are zwitterions in solid state. The new class of compounds-amino enols was synthesized, which similarly to amino acids exists as zwitterions. In obtained cycloadducts amino groups and sugar moieties are close each other and they both are in cis configuration and in axial position. It was also shown that different alkenes can be used as dienophiles towards barbituric acid 5-ylidene alditols, for example, styrene or 1-amino-2-thiocarbamoyl-cyclopent-1-ene.

Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9

A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.

Eco-friendly and ingenious multicomponent synthesis of N-arylquinolines using DABCO/TEAB in water

An easy, improved, and environmentally benign synthesis of N-arylquinolines is reported via one-pot multicomponent reaction of aromatic aldehydes, active methylene compounds and 3-arylamino-5,5-dimethylcyclohex-2-enone utilizing catalytic amount of combin

FeCl3-Catalyzed Combinatorial Synthesis of Functionalized Spiro[Indolo-3,10′-indeno [1,2- b ]quinolin]-trione Derivatives

An efficient, inexpensive, environmentally friendly and high yield one-pot route to new spiro[indolo-3,10′-indeno [1,2-b]quinolin]-trione derivatives has been developed, involving three-component reaction of enaminones, N-substituted isatins and Indane-1,3-dione catalyzed by FeCl3. The approach to this spiro-heterocycle is noteworthy because it results in the formation of three new σ (two C-C and one C-N) bonds in a single operation, leading to the construction of novel spiro skeleton. This method works on a large scale in excellent yields.