Acid Catalyzed Efficient Syntheses of Aryl‐5H‐dibenzo[b,i]xanthene‐5,7,12,14‐(13H)‐tetraones and 3,3‐(Arylmethylene)bis(2‐hydroxynaphthalene‐1,4‐diones) and In Vitro Evaluation of their Antioxidant Activity

Khurana, Jitender M.; Lumb, Anshika; Chaudhary, Ankita; Nand, Bhaskara

doi:10.1002/jhet.1871

Cited by 15 publications

(10 citation statements)

References 18 publications

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“…The characterization of these compounds 3a-f agrees with published data. [12][13][14][15][16][17] Compounds 3g, 3h, and 3i are new ones. On analyzing the 1 H NMR spectra, in general, a singlet at around δ 6.65 to 6.75 ppm corresponded to the aliphatic hydrogen H-9, confirming the synthesis of the compounds.…”

Section: Resultsmentioning

confidence: 99%

“…Due to the broad biological relevance of 3,3´-(arylmethylene) bis (2-hydroxynaphthalene-1,4-diones), considerable efforts have been paid on the improvement of synthetic approaches of this class of compounds for the past decades. Literature methods are mostly based on acid-catalyzed condensation between lawsone and aldehydes using LiCl, 10,11 sulfuric acid, 12 sulfamic acid, 13 camphor sulfonic acid, 14 β -alanine/AcOH, 7 L -aminoacids, 6 and ionic liquilds 15 as catalyst. Several bio-derived catalysts such as lipase, 16 chitosan, and O -carboxymethyl chitosan 17 were employed in these reactions.…”

Section: Introductionmentioning

confidence: 99%

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DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

Giang

Anh

Phương

et al. 2021

Natural Product Communications

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For the first time the 4-dimethylaminopyridine (DMAP) catalyzed straightforward and efficient procedure has been developed for the synthesis of 3,3′-(arylmethylene) bis(2-hydroxynaphthalene-1,4-dione) derivatives starting from lawsone (2-hydroxy-1,4-naphthoquinone) and a variety of (hetero)aromatic aldehydes in ethanol under microwave irradiation. Three of nine synthesized compounds are new. This method provides notable advantages over existing procedures including use of non-traditional basic catalyst and environmentally benign solvent, mild reaction conditions, excellent yields, short reaction time and simple workup.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

Giang

Anh

Phương

et al. 2021

Natural Product Communications

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“…[139] Bis-Lawson can be synthesized by the straightforward reaction of with 2hydroxy-1,4-naphthoquinone and aromatic aldehyde. Some previously reported methodology are β-alanine and acetic acid, [140] TFA, [141] O-carboxymethyl chitosan, [142] Sulfamic acid, [143] H 2 SO 4 or ionic liquid, [144] LiCl, [145] lipase. [146] But till date this field Table 6.…”

Section: Chemistryselectmentioning

confidence: 99%

Humic acid: A Biodegradable Organocatalyst for Solvent‐free Synthesis of Bis(indolyl)methanes, Bis(pyrazolyl)methanes, Bis‐coumarins and Bis‐lawsones

Mitra

Ghosh

2021

ChemistrySelect

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Humic acid, a biodegradable, non‐toxic and easily accessible high molecular weight organocatalyst has been explored for the straightforward and environmentally benign approach towards the preparation of diverse array of functionalized bis(indolyl)methanes, bis(pyrazolyl)methanes, bis‐coumarins and bis‐lawsones by the reaction of a vast range of aldehydes with indole, 3‐methyl‐1‐phenyl pyrazolone, 4‐hydroxycoumarin and 2‐hydroxynaphthalene‐1,4‐dione respectively under solvent‐free condition. These protocols proceed without any hazardous solvents, toxic metal catalysts and harsh reaction conditions. In addition, low catalyst loading, good yield and excellent functional group tolerance are the key advantages of these protocols. The used catalyst and solvent‐free approach make this strategy safe to our mother earth. For the first time reusability of humic acid was investigated and found that it can be recycled up to fifth run without any significant loss of its activity at the end of the reaction. Some bioactive molecules such as arundine, trisindoline and vibribdole A were easily synthesized in our lab by utilizing this designed strategy.

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“…14 30 [Hmim]TFA, 31 pdodecylbenzenesulfonic 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 0 ,N 0 -tetramethylguanidinium triuoroacetate/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 46 1,8-dioxo-octahydroxanthenes have been prepared. In this context, some procedures involving Dowex-50W, 34 1,1,3,3-N,N,N 0 ,N 0 -tetramethylguanidinium triuoroacetate/TFA, 38 graphene oxide-incorporated strontium NPs, 43 choline chloride/ itaconic acid, 44 [Msim]Cl, 47 [Hmim] [HSO 4 ], 47 [Et 3 N-SO 3 4 ], 48 [Bmim] [BF 4 ], 49 Nsulfonic acid poly(4-vinylpyridinium) hydrogen sulfate, 50 p-toluene sulfonic acid, 51 amberlyst-15, 52 and FeCl 3 $6H 2 O 53 have also been reported for the preparation of 5H-dibenzo[b,i]xanthene tetraone materials. Aligned with the manifold capabilities of xanthene derivatives, therefore, the development of simple, efficient and clean synthetic protocols using green and highly reactive environmental benign catalysts is still needed.…”

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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Acid Catalyzed Efficient Syntheses of Aryl‐5H‐dibenzo[b,i]xanthene‐5,7,12,14‐(13H)‐tetraones and 3,3‐(Arylmethylene)bis(2‐hydroxynaphthalene‐1,4‐diones) and In Vitro Evaluation of their Antioxidant Activity

Cited by 15 publications

References 18 publications

DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

Humic acid: A Biodegradable Organocatalyst for Solvent‐free Synthesis of Bis(indolyl)methanes, Bis(pyrazolyl)methanes, Bis‐coumarins and Bis‐lawsones

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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Acid Catalyzed Efficient Syntheses of Aryl‐5H‐dibenzo[b,i]xanthene‐5,7,12,14‐(13H)‐tetraones and 3,3‐(Arylmethylene)bis(2‐hydroxynaphthalene‐1,4‐diones) and In Vitro Evaluation of their Antioxidant Activity

Cited by 15 publications

References 18 publications

DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

Humic acid: A Biodegradable Organocatalyst for Solvent‐free Synthesis of Bis(indolyl)methanes, Bis(pyrazolyl)methanes, Bis‐coumarins and Bis‐lawsones

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

Contact Info

Product

Resources

About

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