Calix[n]arenes: active organocatalysts for the synthesis of densely functionalized piperidines by one-pot multicomponent procedure

Palermo, Valeria; Sathicq, Ángel Gabriel; Liberto, Natália A.; Fernandes, Sérgio Antônio; Langer, Peter; Jios, Jorge L.; Romanelli, Gustavo Pablo

doi:10.1016/j.tetlet.2016.03.090

Cited by 39 publications

(13 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…have been used for the construction of THPD ring. Recently, anionic surfactants sodium dioctylsulfosuccinate (SDOSS), Calix[n]arenes, ethylenediammoniumdiformate (EDDF), cyanuric acid, graphene oxide, polyphosphoric acid supported on silica‐coated magnetic nanoparticles and Bi(III) immobilized on triazine dendrimer stabilized magnetic nanoparticles (Fe 3 O 4 @TDSN−Bi(III)) have been utilized to synthesize this six‐membered nitrogen containing compound. Last year, we published a review article, which uncovered various synthetic strategies developed in the past decade for manufacturing THPD compounds …”

Section: Resultsmentioning

confidence: 99%

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

Khan

Saigal

et al. 2018

ChemistrySelect

View full text Add to dashboard Cite

New and facile one‐pot approach for the syntheses of polysubstituted pyrrol‐2‐one, furan‐2‐one and tetrahydropyridines (THPDs) from easily available starting materials using lemon juice as a green catalyst is presented. The synthesis of diverse furan‐2‐one and pyrrol‐2‐one derivatives were achieved from dialkyl acetylenedicarboxylates, different amines and aldehydes in high yields and short reaction times by employing 0.25 mL of lemon juice at 110 oC under solvent‐free condition. THPDs, on the other hand, were synthesized via the reaction among β‐ketoesters, various aromatic aldehydes, and amines in the presence of 0.25 mL of lemon juice in ethanol at room temperature. The molecular structure of compound pyrrol‐2‐one 7e and THPD 10g were confirmed by the single crystal X‐ray analysis. Application of cheap and green catalyst, environmentally benign reaction condition, good to high yields, applicable to a broad range of substrates and no column chromatographic separation are some salient features of this protocol.

show abstract

Section: Resultsmentioning

confidence: 99%

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

Khan

Saigal

et al. 2018

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…One-pot multicomponent approach fulfils these requirements. [25,26] Literature survey reveals that variety of catalysts have been used to synthesize functionalized piperidines using one-pot multicomponent approach; some of them are listed as: Graphene Oxide, [27] Calix[n]arenes, [28] MgFe 2 O 4 / Cellulose/SO 3 H nanocomposite, [29] Tartaric acid, [24] α-Fe 2 O 3 immobilized benzimidazolium tribromide, [30] Cu(II) grafted SBA-15 functionalized S-Methylisothiourea aminated epibromohydrin, [31] Cyanuric Chloride, [32] Camphor-10-sulfonic acid [33] and so on.…”

Section: Introductionmentioning

confidence: 99%

Autocombustion‐Promoted Synthesis of Lanthanum Iron Oxide: Application as Heterogeneous Catalyst for Synthesis of Piperidines, Substituted Amines and Light‐Assisted Degradations

Pratibha

Rajput

2020

ChemistrySelect

View full text Add to dashboard Cite

An autocombustion technique was adopted to synthesize the Perovskite structured Lanthanum iron oxide nanoparticles (LaFeO3, abbreviated as LFO NPs). This technique offered lots of benefits such as short reaction time along with quick heating rate. LFO NPs were fabricated at different calcination temperatures (300‐800 °C) through the aid of sucrose as chelating agent. The prepared LFO NPs were well characterized by various techniques like X‐ray diffraction (XRD), Fourier transform infrared spectroscopy (FT‐IR), Vibrating sample magnetometer (VSM), Ultraviolet‐Visible spectroscopy (UV‐Vis), Brunauer–Emmett–Teller (BET), X‐ray Photo‐Electron Spectroscopy (XPS) and Transmission electron microscopy (TEM) which affirmed that highly crystalline LFO NPs were obtained at 700 °C. Subsequently, the catalytic activity of the LFO NPs was surveyed for three independent approaches: (i) for the synthesis of functionalized piperidines through activation of carbonyl groups in the reacting partners (ii) for the sunlight‐assisted mineralization of health hazardous food colorant, Allura Red AC (iii) for the hydrogenation of nitro aromatic compounds (NACs) using NaBH4 (sodium borohydride) as source of hydrogen in aqueous medium at room temperature.

show abstract

“…Specially, C‐2 and C‐6 substituted piperidine molecules came from extracts of Dendrobates speciosus (Panamanian poison frogs) have demonstrated various activities such as cytotoxic, antifungal, hemolytic and anti‐HIV properties . Recently, the synthesis of titled compounds were reported using a large number of catalysts, such as bromodimethylsulfonium bromide (BDMS), cerium ammonium nitrate (CAN), p ‐TsOH.H 2 O, tetrabutylammoniumtribromide (TBATB), tartaric acid, Bi (NO 3 ) 3 .5H 2 O, InCl 3 , p ‐sulfonic acid calix[n]arenes, ZrOCl 2 .8H 2 O, I 2 , and sodium dioctyl sulfosuccinate (SDOSS). Herein we report a one‐pot three (is situ five)‐component synthesis of highly functionalized piperidines 7 from the reaction of two equivalents of aromatic aldehyde, two equivalents of aromatic amine, and β ‐ketoester in the presence of Fe/MWCNTs as an efficient, ecofriendly and reusable heterogeneous nanocatalyst in ethanol at ambient temperature (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Application and developing of iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds

Sharghi

Aboonajmi

Mozaffari

et al. 2017

Applied Organom Chemis

View full text Add to dashboard Cite

Iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) is an efficient, ecofriendly and reusable heterogeneous nanocatalyst for the one‐pot synthesis of heterocyclic compounds including bis‐spiro piperidines, piperidines, dihydro‐2‐oxopyrroles, pyrazoles and diazepines at room temperature with good to excellent yields. The heterogeneous nanocatalyst was fully characterized by scanning electron microscopy (SEM), X‐ray diffraction (XRD), inductively coupled plasma (ICP) and FT‐IR analysis. Also, the structures of all prepared compounds were characterized by 1H NMR, 13C NMR, FT‐IR, mass spectrometry (MS) and elemental analysis. The major advantages of these protocols are mild and green reaction conditions, short reaction times, clean reaction, operational simplicity, easy purification and good to excellent yields with the reusable heterogeneous nanocatalyst. The catalyst was ten recycled without significant loss of activity.

show abstract

Calix[n]arenes: active organocatalysts for the synthesis of densely functionalized piperidines by one-pot multicomponent procedure

Cited by 39 publications

References 30 publications

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

Autocombustion‐Promoted Synthesis of Lanthanum Iron Oxide: Application as Heterogeneous Catalyst for Synthesis of Piperidines, Substituted Amines and Light‐Assisted Degradations

Application and developing of iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds

Contact Info

Product

Resources

About