Cyanuric chloride catalyzed metal-free mild protocol for the synthesis of highly functionalized tetrahydropyridines

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.

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

“…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

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.

“…Ramesh et al . synthesized a series of functionalized piperidines via one‐pot, pseudo five‐component condensation of substituted benzaldehydes, anilines and ethyl acetoacetate using a catalytic amount of cyanuric chloride (2,4,6‐trichloro‐1,3,5‐triazine) in ethanol at 80 °C (Scheme ).…”

Section: Organo‐catalyzed Synthesis Of 126‐triaryl‐4‐arylamino‐pipementioning

confidence: 99%

One‐Pot Pseudo Five Component Synthesis of Biologically Relevant 1,2,6‐Triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐ carboxylates: A Decade Update

Kaur¹,

Devi²,

Kumari³

et al. 2018

Piperidines, an important class of N‐heterocycles, are very common in naturally occurring bioactive compounds. Recently, functionalized piperidines, specifically, 1,2,6‐triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐carboxylates have drawn considerable attention due to its diverse pharmacological efficacies that include anti‐cancer, anti‐microbial, anti‐oxidant, anti‐fungal, anti‐inflammatory and acetylcholinesterase (AChE) inhibitory activities. As a result, during the last decade, a number of methods reported for the synthesis of 1,2,6‐triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐carboxylates via one‐pot pseudo five‐component reactions of aromatic aldehydes, anilines and β‐keto esters under various reaction conditions. The present review deals with the ‘‘up to date” developments on the synthesis of 1,2,6‐triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐carboxylates reported so far.