Choline chloride and itaconic acid-based deep eutectic solvent as an efficient and reusable medium for the preparation of 13-aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones

Liu, Peng; Hao, Jian-Wu; Liang, Shao-Juan; Liang, Guang-Li; Wang, Jinyu; Zhang, Zhan‐Hui

doi:10.1007/s00706-015-1571-z

Cited by 29 publications

(3 citation statements)

References 47 publications

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“…The core structure of xanthene exhibits various physicochemical and pharmacological properties such as antiviral, antibacterial, analgesic, antimalarial, anti-inflammatories, and anticancer . Sulfamic acid, pTSA, silica sulfuric acid, molecular iodine, TiO 2 –SO 4 2– , NaHSO 4 –SiO 2 , cyanuric chloride, amberlyst-15, acyclic acidic ionic liquids, core/shell Fe 3 O 4 @GA@isinglass, boric acid, H 5 PW 10 V 2 O 40 /MCM-48, polymeric catalyst, polytungstozincate acid, Fe(OTF) 3 , montmorillonite K10, Ni(ClO 4 ) 2 .6H 2 O, DBH, WCl 6 , Sr(OTF) 2 , proline triflate, TTAB, InCl 3 , TCCA, TMGT, bmim[HSO 4 ], phosphosulfonic acid, [DMEA][PHSO 4 ], sulfamic acid supported on cellulose, zeolites, ion-exchange resins, silica sulfuric acid, Fe 3 O 4 @SiO 2 -SnCl 4 , ChCl/itaconic acid, [CTA]Fe/MCM-41, Fe 3 O 4 @propylsilane@histidine[HSO 4– ], and Fe 3 O 4 @SiO 2 -HPW were used as catalysts for the synthesis of xanthene derivatives . Some reactions catalyzed by them were associated with difficult work up, harsh reaction conditions, poisonous solvents, and low-yield products.…”

Section: Introductionmentioning

confidence: 99%

BioMOF-Mn: An Antimicrobial Agent and an Efficient Nanocatalyst for Domino One-Pot Preparation of Xanthene Derivatives

2022

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In this paper, a new Mn-based metal–organic framework [UoB-6] was obtained via a one-step ultrasonic irradiation method with the ligand (H2bdda: 4,4′-(1,4-phenylenebis(azaneylylidene))bis(methaneylylidene))dibenzoic acid. The structural integrity of the synthesized BioMOF-Mn was corroborated by FT-IR, EDX, ICP, XRD, TEM, DLS, FESEM, and BET-BJH analyses. The aerobic oxidative domino reaction of benzyl alcohols or aldehydes with dimedone derivatives was performed in the presence of the UoB-6 catalyst to produce xanthene derivatives in good yields. Hot filtration and Hg poisoning tests proved the heterogeneous nature of the catalyst. Novel synthesized xanthene-based bis-aldehydes were introduced as potent HDAC1 inhibitors according to molecular docking calculations. Finally, the inhibitory activities of Mn-MOF nanoparticles were evaluated on Escherichia coli and Candida albicans. The MIC, MBC, and MFC values were determined from 2048 to 4096 μg·mL–1 according to antimicrobial susceptibility testing methods. The inhibitory effects of antimicrobial agents can be exacerbated when loaded on BioMOFs.

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Section: Introductionmentioning

confidence: 99%

BioMOF-Mn: An Antimicrobial Agent and an Efficient Nanocatalyst for Domino One-Pot Preparation of Xanthene Derivatives

2022

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“…In general, the straightforward synthesis of 1,8‐dioxooctahydroxanthene involves one‐pot domino Knoevenagel‐Michael reaction of 2 moles of dimedone with 1 mole of aromatic aldehydes. In literature several catalytic systems are reported for their synthesis such as [DDPA][HSO 4 ], [ 22 ] Ni NPs@ N ‐doped titania, [ 23 ] C/TiO 2 ‐SO 3 H, [ 24 ] ZnO, [ 25 ] sulfated zirconia, [ 26 ] Fe 3 O 4 @SiO 2 Imid‐PMA, [ 27 ] β‐cyclodextrin, [ 28 ] Bronsted acidic ionic liquids, [ 29 ] Fe‐Cr‐Ni alloy nano‐belts, [ 30 ] ZnO‐NPs, [ 31 ] alumina‐sulfuric acid, [ 32 ] MSrGO NCs, [ 33 ] Choline chloride, [ 34 ] SmCl 3 , [ 35 ] PDNES, [ 36 ] PVPP‐BF 3 , [ 37 ] PSA, [ 38 ] natural phosphate, [ 39 ] n‐TSA, [ 40 ] Fe 2 (SO 4 ) 3 .7H 2 O, [ 41 ] barium perchlorate, [ 42 ] Ag@CDNS‐N/PMelamine, [ 43 ] sawdust sulphonic acid, [ 12 ] nano‐WO 3 ‐supported sulfonic acid, [ 44 ] CoNP@SBA‐15, [ 45 ] PFPA, [ 46 ] MnFe 2 O 4 , [ 47 ] Fe 3 O 4 @PS@His[HSO 4 − ], [ 48 ] FSM‐16/AEPC‐SO 3 H [ 49 ] and zeolite nanoparticles. [ 50 ]…”

Section: Introductionmentioning

confidence: 99%

An expedient and straightforward solvent‐free synthesis of 1,8‐dioxo‐octahydroxanthenes using eco‐friendly aluminized polyborate catalyst

Aute

Kshirsagar

Uphade

et al. 2020

Journal of Heterocyclic Chem

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The present work deals with a catalytic application of aluminized polyborate as a mild solid acid catalyst for multicomponent synthesis of 1,8-dioxooctahydroxanthenes under solvent-free condition at 100 C-110 C. It involves selective domino Knoevenagel-Michael reaction of 1 mole of aromatic aldehyde with 2 moles dimedone. The aluminized polyborate is simply synthesized by using boric acid and aluminum trichloride and characterized by FT-IR, XRD, SEM and EDAX techniques. The mild Lewis acidity, crystalline solid nature, stability and recyclability are significant features of the catalyst. The solvent-free condition, clean reaction profile, inexpensive and non-toxic catalyst, operational simplicity, good to excellent product yields, reduced reaction time and applicability to wide range of substrate are crucial features of this protocol.

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“… 7 Moreover, some xanthene materials have been used as antagonists for paralyzing the action of zoxalamine 8 and dyes, 9–11 in laser technology, 12 as pH-sensitive fluorescent agents 13 and as bactericides in agriculture. 14 These capabilities indicate the significant impact of xanthenes as the source of valuable drugs and rationalize the immense interest of numerous researchers towards their synthesis; a literature review has shown that using Fe 3 O 4 , 15 ZrO 2 , 16 silica sulfuric acid, 17 (HPO 3 ) n , 18 HOAc, 19 HClO 4 /SiO 2 , 20 PPA/SiO 2 , 20 SbCl 3 /SiO 2 , 21 silica chloride, 22 NaHSO 4 ·SiO 2 , 22 FeCl 3 /SiO 2 , 23 InCl 3 , 18 InCl 3 ·4H 2 O/ionic liquid, 24 In(OTf) 3 , 25 SO 4 2− /TiO 2 , 26 Fe 3 O 4 @SiO 2 @SO 3 H, 27 Fe 3 O 4 @TiO 2 @SO 3 H, 28 ZrO 2 @SO 3 H, 29 n -Bu 4 HSO 4 , 30 [Hmim]TFA, 31 p -dodecylbenzenesulfonic acid, 32 p -dodecylbenzenesulfonic acid/ultrasound, 33 Dowex-50W, 34 amberlyst-15, 35 montmorillonite K10, 36 Fe 3+ -montmorillonite, 37 1,1,3,3- N , N , N ′, N ′-tetramethylguanidinium trifluoroacetate/TFA, 38 Et 3 (PhCH 2 )NBr, 39 TMSCl, 40 DABCO, 41 CuI/poly(4-vinylpyridine), 42 graphene oxide-incorporated strontium NPs, 43 choline chloride/itaconic acid, 44 (NH 4 ) 2 HPO 4 , 45 and polyaniline- p -toluenesulfonate …”

Section: Introductionmentioning

confidence: 99%

Immobilized copper-layered nickel ferrite on acid-activated montmorillonite, [(NiFe₂O₄@Cu)(H⁺-Mont)], as a superior magnetic nanocatalyst for the green synthesis of xanthene derivatives

Zeynizadeh

Rahmani

2019

RSC Adv.

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In this study, the immobilization of copper-layered nickel ferrite on the surface and in the cavities of acidactivated montmorillonite (H + -Mont) was investigated. In this context, magnetic nanoparticles (MNPs) of NiFe 2 O 4 as the prime magnetic cores were prepared. Next, through the reduction of Cu 2+ ions with sodium borohydride, the nanoparticles of Cu 0 were immobilized on the nanocore-surface of NiFe 2 O 4 , and the constituent NiFe 2 O 4 @Cu MNPs were obtained. Moreover, through the activation of montmorillonite K10 (Mont K10) with HCl (4 M) under controlled conditions, the H + -Mont constituent was prepared. The nanostructured NiFe 2 O 4 @Cu was then intercalated within the interlayers and on the external surface of the H + -Mont constituent to afford the novel magnetic nanocomposite (NiFe 2 O 4 @Cu)(H + -Mont). The prepared clay nanocomposite was characterized using FTIR spectroscopy, SEM, EDX, XRD, VSM and BET analyses. The obtained results showed that through acid-activation, the stacked-sheet structure of Mont K10 was exfoliated to tiny segments, leading to a significant increase in the surface area and total pore volume of the H + -Mont constituent as compared to those of montmorillonite alone. SEM analysis also exhibited that the dispersion of NiFe 2 O 4 @Cu MNPs in the interlayers and on the external surface of acid-activated montmorillonite was carried out successfully, and the nanoparticle sizes were distributed in the range of 15-25 nm. The BET surface analysis also indicated that through the immobilization of NiFe 2 O 4 @Cu MNPs, the surface area and total pore volume of the H + -Mont system were decreased. The catalytic activity of (NiFe 2 O 4 @Cu)(H + -Mont) was further studied towards the synthesis of substituted 13-aryl-5H-dibenzo [b,i]xanthene-5,7,12,14(13H) tetraones 3(a-k) and 3,3,6,6-tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H) diones 5(a-k) via the pseudo-one-pot three-component cyclocondensation of 2-hydroxy-1,4-naphthoquinone (Lawsone)/ dimedone and aromatic aldehydes in a mixture of H 2 O-EtOH (1 : 1 mL) as a green solvent at 80-90 C.The (NiFe 2 O 4 @Cu)(H + -Mont) MNPs can be easily separated from the reaction mixture by an external magnetic field and reused for seven consecutive cycles without significant loss of catalytic activity.

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Choline chloride and itaconic acid-based deep eutectic solvent as an efficient and reusable medium for the preparation of 13-aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones

Cited by 29 publications

References 47 publications

BioMOF-Mn: An Antimicrobial Agent and an Efficient Nanocatalyst for Domino One-Pot Preparation of Xanthene Derivatives

BioMOF-Mn: An Antimicrobial Agent and an Efficient Nanocatalyst for Domino One-Pot Preparation of Xanthene Derivatives

An expedient and straightforward solvent‐free synthesis of 1,8‐dioxo‐octahydroxanthenes using eco‐friendly aluminized polyborate catalyst

Immobilized copper-layered nickel ferrite on acid-activated montmorillonite, [(NiFe₂O₄@Cu)(H⁺-Mont)], as a superior magnetic nanocatalyst for the green synthesis of xanthene derivatives

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Choline chloride and itaconic acid-based deep eutectic solvent as an efficient and reusable medium for the preparation of 13-aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones

Cited by 29 publications

References 47 publications

BioMOF-Mn: An Antimicrobial Agent and an Efficient Nanocatalyst for Domino One-Pot Preparation of Xanthene Derivatives

BioMOF-Mn: An Antimicrobial Agent and an Efficient Nanocatalyst for Domino One-Pot Preparation of Xanthene Derivatives

An expedient and straightforward solvent‐free synthesis of 1,8‐dioxo‐octahydroxanthenes using eco‐friendly aluminized polyborate catalyst

Immobilized copper-layered nickel ferrite on acid-activated montmorillonite, [(NiFe2O4@Cu)(H+-Mont)], as a superior magnetic nanocatalyst for the green synthesis of xanthene derivatives

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Immobilized copper-layered nickel ferrite on acid-activated montmorillonite, [(NiFe₂O₄@Cu)(H⁺-Mont)], as a superior magnetic nanocatalyst for the green synthesis of xanthene derivatives