24706-47-6

Upstream product

• 106-47-8 4-chloro-aniline 
• 126-81-8 dimedone 
• 3471-13-4 dimedone 
• 1001588-86-8 7,7-dimethyl-4-phenyl-4,6,7,8-tetrahydro-2H-1,3-benzoxazine-2,5(3H)-dione 

Downstream Products

• 72896-09-4 3-(4-Chloro-phenylamino)-5,5-dimethyl-cyclohex-2-enethione 
• 345926-89-8 N-(4-Chlorphenyl)-5,5-dimethyl-3-(trimethylsiloxy)-2-cyclohexen-1-imin 
• 137556-78-6 methyl 3-(p-chlorophenyl)amino-5,5-dimethyl-1-oxo-2-cyclohexene-2-dithiocarboxylate 
• 137556-82-2 1-(p-chlorophenyl)-7,7-dimethyl-4-methylthio-5-oxo-1,5,6,7-tetrahydro-2H-3,1-benzothiazine-2-thione 

Relevant academic research and scientific papers

A simple method for the rapid synthesis of 2-amino-7,7-dimethyl-5-oxo-1,4-diaryl-hexahydroquinoline-3-carboxamide derivatives

Abstract: Simple synthesis of oxoquinoline carboxamide derivatives via one-pot, multi-component reaction of enaminones derived from the addition of dimedone to various anilines with aromatic aldehydes and cyanoacetamide is described. Optimal reaction cond

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.

Cyclic enaminone as new chemotype for selective cyclooxygenase-2 inhibitory, anti-inflammatory, and analgesic activities

The cyclic enaminone moiety has been identified as a new scaffold for selective inhibition of cyclooxygenase-2 with anti-inflammatory and analgesic activities. The designed cyclic enaminones have been synthesized conveniently through the development of a new catalyst-free methodology and evaluated for cyclooxygenase (COX-1 and COX-2) inhibitory activities. Three compounds 7d, 8, and 9 predominantly inhibited COX-2 with selectivity index of 74.09, 19.45 and 108.68, respectively, and were assessed for in vivo anti-inflammatory activity in carrageenan induced rat paw edema assay. The anti-inflammatory activity of 7d was comparable to that of celecoxib at a dose of 12.5 mg/kg. However, the compounds 8 and 9 were more/equally effective as anti-inflammatory agent compared to celecoxib at the doses of 12.5 mg/kg and 25 mg/kg and also exhibited anti-inflammatory activity comparable to that of diclofenac. The therapeutic potential of the most active compound 9 was further assessed by performing in vivo thermal and mechanical hyperalgesia tests using various models that revealed its analgesic activity. The in vivo non-ulcerogenicity of 9 revealed the gastrointestinal safety as compared to the non-selective COX inhibitor indomethacin. The in vitro antioxidant activity and in vivo experiments on heart rate and blood pressure provided the cardiovascular safety profile of 9. The molecular docking studies rationalize the COX-2 selectivity of the newly found anti-inflammatory compounds 7d, 8, and 9.

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.].

Catalyst-free Synthesis of Tetrahydroacenaphtho[1,2-b]indolone Derivatives via One-pot Four-component Reaction

A simple and efficient one-pot synthesis of tetrahydroacenaphtho[1,2-b]indolone derivatives via four-component reaction of 5,5-dimethylcyclohexane-1,3-dione (dimedone), arylamines, acenaphthoquinone, and active methylene compounds under catalyst-free conditions is described. The reactions were carried out under mild conditions using ethanol as solvent. Advantages of this method include simple experimental and workup procedure, readily available starting materials, and high yields.

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.

Nano fibrous silica sulphuric acid as an efficient catalyst for the synthesis of β-enaminone

Synthesis of KCC-1 silica sulphuric acid as a new catalyst has been reported. The catalyst was characterized using XRD, SEM, TEM, BET, FT-IR, TGA-DTA, and EDX analysis. The catalytic activity was evaluated for the synthesis of enaminones under solvent-free conditions. The catalyst was easily recovered and reused up to seven cycles with slight loss of activity. The attractive features of this protocol are low amount of catalyst loading, short reaction time, mild reaction conditions, good to excellent yield of the products, easy handling of the catalyst and simple operational procedure. Graphical Abstract: [InlineMediaObject not available: see fulltext.]A highly efficient Sulphated nanosilica sulphuric acid has been synthesized and applied for the synthesis of enaminones. This catalytic protocol is better for the synthesis of enaminone than previously reported procedures in terms of catalyst loading, reaction condition, reaction time and yields of the products.