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Relevant academic research and scientific papers

Multi-component synthesis of piperidines and dihydropyrrol-2-one derivatives catalyzed by a dual-functional ionic liquid

N,N,N’,N’-tetramethyl-N,N’-bis(sulfo)ethane-1,2-diaminium mesylate ([TMBSED][OMs]2) was employed for the synthesis of piperidines and dihydropyrrol-2-ones via one-pot multi-component reactions in simple and green processes. This pseudo five-component reaction of aromatic aldehydes, anilines and alkyl acetoacetates was carried out under reflux conditions in ethanol to afford substituted piperidines. Also, dihydropyrrol-2-one derivatives were synthesized by means of four-component reactions of various amines, dialkyl acetylenedicarboxylates and formaldehyde in ethanol at room temperature. The present approaches have several advantages such as good yields, easy work-ups, short reaction times, and utilize mild and clean reaction conditions.

One-pot multicomponent synthesis of tetrahydropyridines promoted by luminescent ZnO nanoparticles supported by the aggregates of 6,6-dicyanopentafulvene

Pot-shaped fluorescent aggregates of 6,6-dicyanopentafulvene derivative 4 serve as reactors and stabilizers for the preparation of luminescent ZnO nanoparticles, which exhibit high catalytic efficiency in one-pot multicomponent synthesis of tetrahydropyridines.

MgFe2O4/cellulose/SO3H nanocomposite: a new biopolymer-based nanocatalyst for one-pot multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones

A new biopolymer cellulose-based magnetic heterogeneous catalyst, MgFe2O4/cellulose/SO3H nanocomposite, was prepared. Fourier-transform infrared spectra, X-ray diffraction, energy-dispersive X-ray, field-emission scanning electron microscopy, thermal analysis (TG, DTG and DSC), dynamic light scattering and vibrating sample magnetometer measurements have been used to characterize the catalyst. Then, it was applied efficiently as an inexpensive and green catalyst in two multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones under solvent-free conditions. The nanocatalyst can be recovered and reused several times without significant loss of catalytic activity.

Bis(1,3-dimethylimidazolidinone) hydrotribromide (DITB) promoted multicomponent reaction for the synthesis of highly functionalized piperidines

A convenient and efficient method has been developed for the synthesis of highly functionalized piperidines via three-component, one-pot domino reaction of β-ketoesters, aromatic aldehydes, and anilines in the presence of catalytic amount of bis(1,3-dimethylimidazolidinone) hydrotribromide (DITB) in ethanol at room temperature.

Alum as an efficient catalyst for the multicomponent synthesis of functionalized piperidines

An effective approach to the synthesis of functionalized piperidines via a one-pot multicomponent reaction of aniline, β-ketoester and aldehyde in the presence of alum as an efficient catalyst has been reported. The present procedure offers advantages such as simple workup, short reaction time and offers rapid access to a variety of functionalized piperidines.

Multicomponent synthesis of highly functionalized piperidines using sulfamic acid as a heterogeneous and cost effective catalyst

Sulfamic acid has been found as an efficient and cost effective catalyst for one pot multicomponent synthesis of some new densely functionalized piperidine derivatives using amines, aldehydes and β-keto esters. The meritorious aspects of this novel protocol are atom economic process, heterogeneous and easily accessible catalyst, good to excellent yield, convenient work up and eco-friendly route.

L-Proline nitrate: A recyclable and green catalyst for the synthesis of highly functionalized piperidines

The synthesis of highly functionalized piperidines has been strategically accessed via organo-catalytic three components (in situ five components) reaction of an amine, aldehyde and 1,3-dicarbonyl compound. This imine based multi-component reaction was realized using fully green l-proline nitrate as recyclable room temperature ionic liquid. Recycling of the catalyst was possible up to five runs without loss of catalyst activity. Smaller E-factor (0.255) and process mass intensity (PMI = 3.35), high atom-economy (AE = 89.5%) and reaction mass efficiency (RME = 79.66%) demonstrates the higher environmental compatibility and sustainability of this protocol. DFT calculations showed that the l-proline catalyzed reaction proceeds by three pathways; (i) via proline enamine pathway, (ii) proline mediated aniline enamine pathway or (iii) the pathway involving iminium activation of the aldehyde to provide the Knoevenagel product. This journal is

Polyphosphoric acid-zirconia pillared clay composite catalytic system for efficient multicomponent one pot synthesis of tetrahydropyridines under environmentally benign conditions

A series of zirconia pillared clay-polyphosphoric acid (PPA) composites are synthesized by adopting different preparative strategies. Initially, PPA is intercalated to the clay matrix with and without the use of structure expanding agent (CTAB). Subsequently, the PPA-clay composite is pillared with Zr-polycation to form the composite materials. In an alternate approach, Zr-pillared clay is synthesized by insertion of Zr-polycation, which is then used for dispersion of PPA moiety in the pillared clay matrix. The synthesized composites are characterized by XRD, FTIR, UV-vis, TGA, EDX, FE-SEM and sorptometric techniques. XRD study indicated an expansion in the clay structure after intercalation of PPA as well as the Zr-polycations. The FTIR spectra exhibit characteristic vibrational features of the clay sheet as well as PPA moiety indicating the structural stability of the composite materials. The phosphorous content in the composite samples is analyzed using EDX study. FE-SEM study indicated morphological changes upon intercalation of PPA and Zr-polycations to the clay matrix. The catalytic activity of the composite catalysts has been examined for the synthesis of tetrahydropyridines under environmental benign conditions by one pot multicomponent condensation of β-dicarbonyl compounds, substituted anilines and substituted benzaldehydes. The PPA intercalated clay pillared with Zr polycations (PPA-ZrP) is found to be highly efficient for the synthesis of structurally diverse substituted tetrahydropyridines under mild conditions.

Fe(NO3)3·9H2O as efficient catalyst for one-pot synthesis of highly functionalized piperidines

Fe(NO3)3·9H2O is used as an efficient and effective catalyst for the one-pot three-component synthesis of highly functionalized piperidines from aromatic aldehydes, anilines and β-ketoesters in ethanol at ambient temperature. This procedure includes some important aspects like the easy work-up, no need to column chromatography, simple and readily available precursors, and good to high yields.

Magnetically recyclable magnetite-ceria (Nanocat-Fe-Ce) nanocatalyst-applications in multicomponent reactions under benign conditions

A novel magnetite nanoparticle-supported ceria catalyst (Nanocat-Fe-Ce) has been successfully prepared by a simple impregnation method and was characterized by XRD, SIMS, FEG-SEM-EDS, and TEM. The exact nature of Nanocat-Fe-Ce was confirmed by X-ray photoelectron spectroscopy and it is noted that CeO2 nanoparticles are supported on magnetite, with evidence of secondary ion mass spectrometry. Catalytic activity of the nano-catalyst was explored for the synthesis of dihydropyridines under benign conditions; a greener protocol is described that provides a simple and efficient method for the synthesis of functionalized 1,4-dihydropyridines using a recyclable nanocatalyst. Notably, 5.22 mol% of the catalyst is sufficient to catalyze the multicomponent reaction in ethanolic medium at room temperature. Importantly, the catalyst could be easily separated from the reaction mixture by using an external magnet and recycled several times without loss of activity.