24706-49-8Relevant academic research and scientific papers
Molecular iodine-catalyzed mild and effective synthesis of β-enaminones at room temperature
Datta, Bandita,Reddy, M. B. Madhusudana,Pasha
, p. 2331 - 2336 (2011)
Molecular iodine has been found to be an efficient and ecofriendly catalyst for the synthesis of β-enaminones from dimedone and amines at room temperature in the presence of acetonitrile within 60 min. The experimental procedure is simple, includes shorter reaction times, and results in excellent yields of the products. Copyright
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.
Design, synthesis and biological evaluation of novel α-acyloxy carboxamides via Passerini reaction as caspase 3/7 activators
Salah Ayoup, Mohammed,Wahby, Yasmin,Abdel-Hamid, Hamida,Ramadan, El Sayed,Teleb, Mohamed,Abu-Serie, Marwa M.,Noby, Ahmed
, p. 340 - 356 (2019/03/04)
Evasion of apoptosis is a hallmark of cancer. Caspases; the key executors of apoptotic cascade are attractive targets for selective induction of apoptosis in cancer cells. Within this approach, various caspase activators were introduced as lead anticancer agents. In the current study, a new series of multifunctional Passerini products was synthesized and evaluated as potent caspase-dependent apoptotic inducers. The synthetic strategy adopted this isocyanide-based multicomponent reaction to possibly mimic the pharmacophoric features of various lead apoptotic inducers, where a series of α-acyloxy carboxamides was prepared from p-nitrophenyl isonitrile, cyclohexanone and various carboxylic acids. Accordingly, the main amide-based scaffold was decorated by substituents with varying nature and size to gain more information about structure-activity relationship. All the synthesized compounds were screened for cytotoxicity against normal human fibroblasts and their potential anticancer activities against three human cancer cell lines; MCF-7 (breast), NFS-60 (myeloid leukemia), and HepG-2 (liver) utilizing MTT assay. Among the most active compounds, 13, 21 and 22 were more potent and safer than doxorubicin with nanomolar IC50 values and promising selectivity indices. Mechanistically, 13, 21 and 22 induced apoptosis by significant caspase activation in all the screened cancer cell lines utilizing flow cytometric analysis and caspase 3/7 activation assay. Again, 13 and 21 recorded higher activation percentages than doxorubicin, while 22 showed comparable results. Apoptosis-inducing factor1 (AIF1) quantification assay declared that 13, 21 and 22 didn't mediate apoptosis through AIF1-dependent pathway (i.e. only by caspase activation). Physicochemical properties, pharmacokinetic profiles, ligand efficiency metrics and drug-likeness data of all the synthesized compounds were computationally predicted and showed that 13, 21 and 22 could be considered as drug-like candidates. Finally, selected compounds were preliminarily screened for possible antimicrobial activities searching for dual anticancer/antimicrobial agents as an advantageous approach for cancer therapy.
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.
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.
Nano fibrous silica sulphuric acid as an efficient catalyst for the synthesis of β-enaminone
Siddiqui, Zeba N.,Khan, Kulsum,Ahmed, Nayeem
, p. 623 - 632 (2014/04/03)
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.
A mild and efficient method for synthesis of β-enaminones using melamine-formaldehyde resin supported H+ under solvent free conditions
Rezaei, Ramin,Shakeri, Mozhdeh
, p. 7079 - 7082 (2013/08/23)
A green and efficient practical approach is developed for the synthesis of β-enaminones using melamine-formaldehyde resin supported H+ (MFRH) as a mild and inexpensive catalyst in solvent-free media. The present method was performed by combining low cost and readily available amines, 1,3-dicarbonyls and melamine-formaldehyde resin supported H+ (MFRH) as a catalyst. This method is applicable to both cyclic and acyclic ketones with aromatic and aliphatic amines, and provides several advantages such as environmental friendliness, low cost, good yields and simple workup procedure.
Efficient PPA-SiO2-catalyzed synthesis of β-enaminones under solvent-free conditions
Nisar, Muhammad,Ali, Ihsan,Shah, Muhammad Raza,Qayum, Mughal,Zia-Ul-Haq, Muhammad,Rashid, Umer,Islam, Md. Saiful
, p. 15182 - 15192 (2014/01/17)
An efficient method has been developed for the synthesis of β-enaminones under solvent-free reaction conditions using PPA-SiO2 as catalyst. The reaction yields were good to excellent (up to 90%). This methodology affords high selectivity and good tolerance of a variety of different functional groups present on both aromatic and aliphatic amines. In addition, the methodology is environmentally benign and cost-effective due to absence of solvent and easy work-up.
Silica sulfuric acid-mediated synthesis of β-enaminones and β-enaminoesters under microwave irradiation
Datta, Bandita,Pasha
experimental part, p. 171 - 177 (2011/04/22)
Silica sulfuric acid, a heterogeneous reagent, has been found to be an efficient catalyst for the synthesis of β-enaminones and β-enaminoesters under microwave irradiation in a microwave reactor within 2 min. The experimental procedure is simple and environment-friendly, and results in excellent yields of the products. Further, the catalyst is recyclable, and the reaction is 60 times faster than the reaction at room temperature. Copyright Taylor & Francis Group, LLC.
An improved method for the synthesis of carbazolones by palladium/copper-catalyzed intramolecular annulation of n -arylenaminones
Weng, Bojie,Liu, Rui,Li, Jing-Hua
experimental part, p. 2926 - 2930 (2010/10/18)
An improved method for the synthesis of carbazolones via the condensation of arylamines with 1,3-cyclodiketones followed by intramolecular oxidative cyclization catalyzed by palladium acetate and copper acetate in ethanol under an oxygen atmosphere was established. The improved method has the advantage of easily available starting materials and affords good yields.
