18940-21-1Relevant academic research and scientific papers
Synthesis of new heterocyclic systems—substituted spiro[chromene-4,3′-indoles] and spiro[indole-3,4′-quinolines]
Pogosyan,Avakimyan, Dzh. A.,Stepanyan
, p. 1308 - 1311 (2016)
Methods have been developed for the synthesis of new heterocyclic systems, spiro[chromene-4,3′- indoles] and spiro[indole-3,4′-quinolines] by the base-catalyzed domino reaction of isatins with 5,5-dimethylcyclohexane- 1,3-dione (or 5,5-dimethyl-3-anilinoc
Synthesis, 1H, 13C and 15N NMR study of Azo coupling products from enaminones
Simunek, Petr,Lycka, Antonin,Machacek, Vladimir
, p. 2764 - 2769 (2002)
Compounds 2 were prepared by the reaction of 3-amino-5,5- dimethylcyclohex-2-en-1-one and its N-phenyl derivative with substituted benzenediazonium tetrafluoroborates, and their 1H, 13C and 15N NMR spectra were measured and analysed. The active components react with enaminones in molar ratios of 2:1. Only in the case of 4-methoxybenzenediazonium tetrafluoroborate and 3-amino-5,5-dimethylcyclohex-2-en-1-one were traces of the product of the 1:1 reaction observed. The attack by the diazonium component occurs at carbon atoms C-2 and C-4, and the hydrazo form is always formed at the 2-position. 15N NMR spectroscopy was adopted to study the position of the tautomeric equilibrium (arylazo -arylhydrazono) at the 4-position: This equilibrium depends predominantly on the substituents of the amino group and, to a lesser extent, on the substituents of the diazonium component. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Efficient Synthesis of a Series of Novel Octahydroquinazoline-5-ones via a Simple on-Water Urea-Catalyzed Chemoselective Five-Component Reaction
Zheng, Sichao,Zhong, Shufang,Chen, Zhipeng,Chen, Wenhua,Zhu, Qiuhua
, p. 475 - 481 (2016)
Multicomponent reactions (MCRs) have become a powerful tool for drug discovery and development owing to their advantages of fast and efficient construction of a large library of products with complexity and diversity. However, conventional MCRs usually pr
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.
A simple method for the rapid synthesis of 2-amino-7,7-dimethyl-5-oxo-1,4-diaryl-hexahydroquinoline-3-carboxamide derivatives
Hosseini, Fahimeh Sadat,Bayat, Mohammad
, p. 2267 - 2274 (2020/05/19)
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
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.
Photocyclization to cis-Hexahydrocarbazol-4-ones: Substrate Modification, Mechanism, and Scope
Modha, Sachin G.,P?thig, Alexander,Dreuw, Andreas,Bach, Thorsten
, p. 1139 - 1153 (2019/01/30)
Upon irradiation at = 366 nm, tertiary N-alkoxycarbonyl-N-aryl-β-enaminones furnished exclusively the trans-hexahydrocarbazol-4-ones by a conrotatory [6π] photocyclization but epimerized on silica to cis-hexahydrocarbazol-4-ones (14 examples, 44-98% yield). The acceptor substitution on the nitrogen atom enhanced the stability of the cyclized products compared to N-alkyl-N-aryl-β-enaminones reported previously. The mechanism of the [6π] photocyclization was investigated by quenching experiments, deuterium-labeling experiments, and DFT calculations, suggesting a triplet pathway for the conrotatory ring closure followed by a suprafacial [1,4] hydrogen migration.
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.
Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis
Bhattacherjee, Dhananjay,Ram, Shankar,Chauhan, Arvind Singh,Yamini,Sheetal,Das, Pralay
supporting information, p. 5934 - 5939 (2019/04/08)
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
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.].
