Nanocrystalline Cu–ZnO as an Green Catalyst for One Pot Synthesis of 4,4′-((phenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) Derivatives

Shinde, Santosh T.; Karale, B. K.; Bankar, Digambar B.; Arbuj, Sudhir S.; Moulavi, Mansur; Amalnerkar, Dinesh; Kim, Taesung

doi:10.1166/jnn.2019.16490

Cited by 6 publications

(2 citation statements)

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“…White solid; R f = 0.54 (30% EtOAc/70% hexane); mp = 172–175 °C (lit. mp = 175–177 °C); 61 1 H NMR (CDCl 3 , 400 MHz): δ 11.96 (br s, 2H), 6.75 (d, J = 8.0 Hz, 1H), 6.60 (d, 2H), 5.49 (s, 1H), 3.83 (s, 3H), 3.74 (s, 3H), 2.36 (m, 8H), 1.23 (s, 6H), 1.21 (s, 6H); 13 C NMR (CDCl 3 , 100 MHz): δ 204.8, 195.5, 148.7, 147.1, 134.1, 118.8, 115.7, 111.6, 54.4, 52.4, 47.1, 31.2, 29.8, 27.0; MS (APCI) m / z : [M + H] + calcd for C 25 H 33 O 6 428, found; IR V max = 2931, 1720, 1581, 1458, 1242, 1149, 1026, 871, 840, 763, 663 cm –1 .…”

Section: Methodsmentioning

confidence: 99%

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

et al. 2022

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A simple, straightforward, and energy-efficient greener route for the synthesis of a series of biologically interesting functionalized 1,1-dihomoarylmethane scaffolds has been developed in the presence of meglumine as an efficient and eco-friendly organo-catalyst via one-pot pseudo-three-component reaction at room temperature. Following this protocol, it is possible to synthesize 1,1-dihomoarylmethane scaffolds of an assortment of C–H activated acids such as dimedone, 1,3-cyclohexadione, 4-hydroxy-6-methyl-2-pyrone, 4-hydroxycoumarin, and 1-phenyl-3-methyl-pyrazolone. The salient features of the present green protocol are mild reaction conditions, good to excellent yields, operational simplicity, easy isolation of products, no cumbersome post treatment, high atom economy, and low E-factor. In addition, this chemistry portrays several green advantages including the reusability of reaction media and product scalability, which makes protocol sustainably efficient. Additionally, several control experiments such as protection of catalyst reactive site, D 2 O exchange, and 1 H NMR studies revealed possible pathways for meglumine-promoted reactions. Inspired by the natural physiological environment of 1,1-dihomoarylmethane scaffolds, we reconnoitered the biological profile of our compounds and synthesized compounds that were promising for their antiproliferative and antibacterial activities.

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Section: Methodsmentioning

confidence: 99%

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

et al. 2022

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“…Literature survey shows that the most common method for the synthesis of 4,4'-(phenylmethylene) bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) is the condensation of aldehydes with 3methyl-1-phenyl-5-pyrazolone. Several catalysts have been used for this reaction including Mohr's Salt, [25] Ni-guanidine@MCM-41 NPs, [26] PEG-400, [27] silica sulfuric acid, [28] sulfonated rice husk ash (RHA-SO 3 H), [29] sulfuric acid ([3-(3silicapropyl)sulfanyl]propyl)ester, [30] tetrakis(N-methylimidazolium-1-ylmethyl)methane tetra hydrogen sulfates, [31] Xanthan sulfuric acid, [32] [Et 3 NH][HSO 4 ], [33] 1-(carboxymethyl)pyridinium chloride {[cmpy]Cl}, [34] Na + -MMT-[pmim]HSO 4 , [35] cage like CuFe 2 O 4 hollow nanostructure, [36] Chitosan-SO 3 H (CTSA), [37] DCDBTSD, [38] guanidine hydrochloride, [39] lemon juice, [40] Mn-lysine complex on magnetic nanoparticles, [41] NPS-γ-Fe 2 O 3 , [42] SDBS, [43] K 2 CO 3 , [44] Pyridine trifluoroacetate, [45] Phosphomolybdic acid, [46] L-Proline, [47] Cu-ZnO, [48] ChCl:TA, [49] chickpea leaf exudates (CLE), [50] ZnO NPs, [51] and BPHCSF [52] However, most of these synthetic methods display some disadvantages such as employing strong acidic conditions, toxic reagents, expensive catalysts, tedious workup procedures, harsh reaction conditions, and low yields of the products that restrict their usage in practical applications. Considering these lacunas with already reported synthetic protocols, there is still scope for designing a suitable synthetic protocol, which is environmentally benign.…”

Section: Introductionmentioning

confidence: 99%

Greener Synthetic Approach for 4,4′‐(Arylmethylene)bis(3‐methyl‐1H‐pyrazol‐5‐ol) Derivatives in an Aqueous Medium using Theophylline as a Catalyst

Pund,

Dhumal,

Deshmukh

et al. 2023

ChemistrySelect

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Herein, we report an efficient, convenient and environmentally benign method for the synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1H‐pyrazol‐5‐ol) derivatives. The reaction of aromatic aldehydes with 3‐methyl‐1‐phenyl‐5‐pyrazolone or 5‐methyl‐2,4‐dihydro‐3H‐pyrazol‐3‐one in the presence of theophylline catalyst delivered the series of bis‐pyrazole compounds in very high yields. The method has successfully demonstrated the utility of theophylline as an expedient, eco‐friendly and green catalyst in an aqueous medium.

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Zirconium@guanine@MCM‐41 nanoparticles: An efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component tandem Knoevenagel condensation–Michael addition–cyclization Reactions

Nikoorazm

Mohammadi

Khanmoradi

2020

Applied Organom Chemis

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MCM-41-supported nanoscale guanine bonded with Zr (IV) was prepared using sol-gel method and characterized by FT-IR, Raman, XRD, BET, TGA, EDX, ICP, AAS, X-Ray mapping, SEM and TEM techniques. This compound was employed as an efficient, chemoselectivity and green heterogeneous catalyst in order to prepare a series of benzo[a]benzo[6,7]chromeno[2,3-c] phenazine and spiro[benzo[a]benzo[6,7]chromeno[2,3-c] phenazine] derivatives by one-pot, four-component domino reaction from the 2-hydroxy-1,-4-naphthoquinone, benzene-1,2-diamines, 2-hydroxy-1,4-naphthoquinone and carbonyl compounds in PEG, at 100 C and, also, Bis (pyrazolyl) methane derivatives using aldehydes and 3-Methyl-1-phenyl-5-pyrazolone in ethanol under reflux condition. Results indicated that all products were synthesized in short reaction times and high yields in the ranges 78-99%. The Zr-guanine-MCM-41 can be recycled four runs without any significant loss of its catalytic activity. In addition, the stability of the catalyst was confirmed by metal leaching, heterogeneity tests, SEM and FT-IR techniques. K E Y W O R D S benzo[a]benzo[6,7]chromeno[2,3-c]phenazines, Bis (pyrazolyl)methanes, Spiro[benzo[a] benzo[6,7]chromeno[2,3-c] phenazine], Tandem Knoevenagel condensation-Michael additioncyclization, Zr-guanine-MCM-41

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Nanocrystalline Cu–ZnO as an Green Catalyst for One Pot Synthesis of 4,4′-((phenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) Derivatives

Cited by 6 publications

References 0 publications

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

Greener Synthetic Approach for 4,4′‐(Arylmethylene)bis(3‐methyl‐1H‐pyrazol‐5‐ol) Derivatives in an Aqueous Medium using Theophylline as a Catalyst

Zirconium@guanine@MCM‐41 nanoparticles: An efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component tandem Knoevenagel condensation–Michael addition–cyclization Reactions

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