24706-48-7Relevant articles and documents
Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction
Biswas, Nandita,Srimani, Dipankar
, p. 9733 - 9743 (2021/07/20)
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.
Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property
Kundu, Tania,Pramanik, Animesh
, (2020/03/13)
Diminution of oxidative stress-mediated diseases is an essential pharmaceutical objective in modern biomedical research. The present work stresses upon the efficient and eco-friendly synthesis of an array of novel diversely functionalized pyrrole derivatives which are found to be antioxidants with reactive oxygen species (ROS) shielding competency against the deleterious consequence of oxidative stress. The results of the investigation displayed the effect of structural modification of the pyrrole derivatives on their respective antioxidant properties to various ROS. Noteworthy, the pyrrole moiety bearing 4-hydroxycoumarin or 2-hydroxy-1,4-naphthoquinone as substituent showed outstanding defensive potency towards [rad]OH and O2 [rad] ? while, nitrogen atom linked with aliphatic side-chain in the pyrrole scaffold made a strong affirmative impression in DPPH[rad] scavenging assay. More interestingly, an influencing reducing power was observed in pyrrole derivatives carrying cyclohexane 1,3-dione as one of the substituents. To have a comprehensive acuteness into the antioxidant capacity of the synthesized pyrrole derivatives against Trolox as a standard antioxidant, a crucial approach was taken into account by calculating TEAC (Trolox Equivalent Antioxidant Capacity) in case of [rad]OH and DPPH[rad] scavenging activity.
Metal-free syntheses of new azocinesviaaddition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols
Arimitsu, Satoru,Genta, Kojya,Mohammadizadeh, Mohammad Reza,Mousavi, S. Hekmat,Poorsadeghi, Samira,Saberi, Dariush
, p. 20552 - 20557 (2020/06/22)
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
Mousavi, Seyyed Rasul,Sereshti, Hassan,Rashidi Nodeh, Hamid,Foroumadi, Alireza
, (2018/10/26)
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.
β-Enaminones over recyclable nano-CoFe2O4: a highly efficient solvent-free green protocol
Eidi, Esmaiel,Kassaee, Mohamad Z.,Cummings, Peter T.
, p. 5787 - 5799 (2018/05/14)
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
Bayat, Mohammad,Amiri, Zeinab
, p. 1346 - 1351 (2018/04/14)
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.
Gold catalyzed synthesis of tetrahydropyrimidines and octahydroquinazolines under ball milling conditions and evaluation of anticonvulsant potency
Vadivelu,Raheem,Sugirdha,Bhaskar,Karthikeyan,Praveen
supporting information, p. 90 - 101 (2018/02/07)
A fast, mechanochemical and solvent-free synthesis of substituted tetrahydropyrimidines and octahydroquinazolines under Au(III)-catalysis has been developed. The practical feasibility, eco-friendliness and operational simplicity of this chemistry is exemplified by ball milling three components such as formaldehyde, amines and 2-butynedioates/dimedone in a shaker mill for as little as five minutes, thus avoiding the requirement of undesirable solvents and long reaction times. Moreover, this protocol furnishes the target compounds in high yields without any side products and in some cases offers products with excellent regioselectivity. Out of the 26 compounds screened for anticonvulsant potency, 11 compounds exhibited comparable activity against a standard drug.
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
Pa?asz, Aleksandra,Ciez, Dariusz,Musielak, Bogdan,Kalinowska-T?u?cik, Justyna
, p. 8911 - 8924 (2015/11/02)
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
Lobo, Gricela,Monasterios, Melina,Rodrigues, Juan,Gamboa, Neira,Capparelli, Mario V.,Martínez-Cuevas, Javier,Lein, Michael,Jung, Klaus,Abramjuk, Claudia,Charris, Jaime
, p. 281 - 295 (2015/04/27)
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.
FeCl3-Catalyzed Combinatorial Synthesis of Functionalized Spiro[Indolo-3,10′-indeno [1,2- b ]quinolin]-trione Derivatives
Mondal, Animesh,Mukhopadhyay, Chhanda
supporting information, p. 404 - 408 (2016/01/15)
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.
