Efficient One-Pot Three-Component Synthesis of 3,4,5-Substituted Furan-2(5 H )-ones Catalyzed Watermelon Juice

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: Introductionmentioning

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

“…the existence of many different components of citrus limonium, including moisture (85 %), sugars (11.2 %), citric acid (5‐7 %), protein (1 %), vitamin‐C (0.5 %), fat (0.9 %), minerals (0.3 %), fibers (1.6 %) and some other organic acids can be a main drawback of the use of lemon juice as a catalyst, which can cause many by‐products and leakage of its components in products. Long‐time heating of natural chemicals and juices can cause significant changes in their components and chemical structure, therefore, their recycling is impossible [55,56,59] . Green synthesis of 3,4,5‐substituted furan‐2(5H)‐ones were reported using β‐cyclodextrin which is a recyclable cyclic oligosaccharide catalyst [53,60] .…”

Section: Resultsmentioning

confidence: 99%

“…There are different reported catalytic methodologies for preparing 3,4,5‐trisubstituted furan‐2‐ones, including (a) metal‐containing catalysts and nanoparticles such as SnCl 2 .2H 2 O, [38] ZnO nanoparticles, [47] SnO nanoparticles, [48] HY Zeolite nano‐powder, [49] 4‐Carboxybenzyl sulfamic acid functionalized Fe 3 O 4 nanoparticles, [50] (b) organic salts prepared by strong inorganic acid such as sulfuric acid [Bu 4 N][HSO 4 ], [51] N‐methyl 2‐pyrrolidonium hydrogen sulfate ([H‐NMP]HSO 4 ), [52] (c) natural chemicals such as β‐cyclodextrin, a cyclic oligosaccharide, [53] sucrose, [54] watermelon juice, [55] barberry juice, [56] Vitamin B12 [43] and (c) carbonous catalysts such as graphene oxide (GO) nanosheet [58] (Table 3).…”

Section: Resultsmentioning

confidence: 99%

“…Long-time heating of natural chemicals and juices can cause significant changes in their components and chemical structure, therefore, their recycling is impossible. [55,56,59] Green synthesis of 3,4,5-substituted furan-2(5H)-ones were reported using β-cyclodextrin which is a recyclable cyclic oligosaccharide catalyst. [53,60] Long reaction time and costly purification of products can be mentioned as drawbacks on an industrial scale.…”

Section: Comparing the Current Catalytic System With Some Reported Pr...mentioning

confidence: 99%

“…There are different reported catalytic methodologies for preparing 3,4,5-trisubstituted furan-2-ones, including (a) metal-containing catalysts and nanoparticles such as SnCl 2 .2H 2 O, [38] ZnO nanoparticles, [47] SnO nanoparticles, [48] HY Zeolite nanopowder, [49] 4-Carboxybenzyl sulfamic acid functionalized Fe 3 O 4 nanoparticles, [50] (b) organic salts prepared by strong inorganic acid such as sulfuric acid [Bu 4 N][HSO 4 ], [51] N-methyl 2-pyrrolidonium hydrogen sulfate ([H-NMP]HSO 4 ), [52] (c) natural chemicals such as β-cyclodextrin, a cyclic oligosaccharide, [53] sucrose, [54] watermelon juice, [55] barberry juice, [56] Vitamin B12 [43] and (c) carbonous catalysts such as graphene oxide (GO) nanosheet [58] (Table 3). Despite the effectiveness of these catalysts, the usage of some of these methods are allied with several shortcomings such as harsh reaction conditions, and use of toxic solvents and waste generation during catalyst preparation, [58] the use of expensive catalyst, [57] possible leakage transition metal-containing catalysts, [58] prolonged reaction time, [49,53] difficulty in product isolation and purification, [53] the use of corrosive inorganic acids for preparing catalysts, [51,52] lack recyclability of catalysts, [59] and co-occurrence of side reactions.…”

Section: Comparing the Current Catalytic System With Some Reported Pr...mentioning

confidence: 99%

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A More Sustainable and Greener Process for Preparing 3,4,5‐Trisubstituted Furan‐2‐one Derivatives

Zaharani,

Ghafarikhaligh,

Khaligh

2023

Treatment of 4,4′‐trimethylenedipiperidine with two equivalents of glacial acetic acid gave a cream‐like liquid with a pale yellow color. Then, its ionic chemical structure was demonstrated by different spectroscopic techniques. The thermal behavior of the new ionic liquid was also studied by TGA/DTA and DSC techniques to record its phase transitions and thermal stability and compare those with another analog, i. e., 1H,4H‐piperazine‐N,N′‐diium diacetate. Then, the multicomponent condensation of halogen‐substituted benzaldehydes with dimethyl 2‐(phenylamino) fumarate was investigated using the new ionic liquid in ethanol, an eco‐friendly medium. Excellent yield with 100 % conversion was obtained and pure products could be isolated directly from ethanol. After separating pure products, the residue solution was employed in the next run without separation, concentration, purification, or activation. Furthermore, the synthesis of methyl 2‐(4‐chlorophenyl)‐5‐oxo‐4‐(phenylamino)‐2,5‐dihydro‐furan‐3‐carboxylate was carried out on a large scale using the current catalytic process, affording a conversion of 100 % and a high yield of the crystalline product even after ten consecutive runs. Energy efficiency, cost‐ and time‐saving, and waste prevention demonstrate the newly developed metal‐ and halogen‐free catalysis as a more sustainable catalytic process for preparing 3,4,5‐trisubstituted furan‐2‐one derivatives on the laboratory and industrial scale.

One‐pot Expedient Green Synthesis of N‐benzhydrylpyridine‐2‐amines Using Gooseberry Amla Fruit Extract (GAFE): A Naturally Occurring Organocatalyst

Nadoni,

Kamble,

Metre

et al. 2024

One‐pot synthesis of N‐benzhydrylpyridine‐2‐amines employing Gooseberry amla (Phyllanthus emblica) fruit extract (GAFE) as an organoacid catalyst, was executed in the current investigation with the primary emphasis on green chemistry. The spectrum displays of these compounds were analyzed using FT‐IR, 1H and 13C NMR, and LC‐MS. For substantial ecological assurance, we adopted green chemistry methodologies to lessen the risk of exposure to hazardous chemical materials amid the synthesis of diverse heterocyclic compounds. Moreover, these α‐branched amines are synthesized in the greener and milder way with the use of a natural organoacid with more yields compared with the other chemical methods. This innovative approach has a lot to offer in terms of its rapid reaction time frames, clear reaction profiles, benign reaction conditions, absence of toxic catalysts and risky solvents, accessibility of the work‐up process, and greater yield.