Ionic liquid catalyzed one-pot synthesis of spiropyran derivatives via three-component reaction in water

Jin, Shi; Ding, Maohua; Guo, Hongyun

doi:10.1515/hc-2012-0159

Cited by 9 publications

(5 citation statements)

References 20 publications

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“…To present the advantages of our novel catalyst, its catalytic activity was compared with the other catalysts reported for the aforementioned MCRs, hitherto (Table 11 ). The catalytic potency of our novel catalyst (PC/AgNPs) was compared with the same recently reported MCR, involving acenaphthenequinone, malononitrile and dimedone for the preparation of 2′-amino-tetrahydro-2 H -spiro[acenaphthylene-1,4′-chromene]-3′-carbonitrile ( 12b ) with various catalysts such as CaCl 2 , 164 Fe 3 O 4@ Cs-SO 3 H, 163 Na 2 EDTA, 165 HAuCl 4 .3H 2 O, 166 Meglumine, 135 Fe 2 O 3, 167 HEAA, 168 Cu(OAc) 2 . H 2 O, 169 Amb-400Cl (IRA-400 Cl), 170 Fe 3 O 4 @CS-SO 3 H NPs, 171 C 4 (DABCO-SO 3 H) 2 .…”

Section: Resultsmentioning

confidence: 83%

Silver nanoparticles-decorated Preyssler functionalized cellulose biocomposite as a novel and efficient catalyst for the synthesis of 2-amino-4H-pyrans and spirochromenes

Saneinezhad

Mohammadi

Zadsirjan

et al. 2020

Sci Rep

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Silver nanoparticles-decorated Preyssler functionalized cellulose biocomposite (PC/AgNPs) was prepared and fully characterized by FTIR, UV–vis, SEM, and TEM techniques. The preparation of PC/AgNPs was studied systematically to optimize the processing parameters by Taguchi method using the amount of PC, reaction temperature, concentration of silver nitrate and pH of medium. Taguchi’s L9 orthogonal (4 parameters, 4 level) was used for the experimental design. The SEM analysis confirmed the presence of the Preyssler as a white cloud as well as spherical AgNPs on the surface of cellulose. The formation of AgNPs on the surface was observed by changing of the color from yellow to deep brown and confirmed by UV–vis spectroscopy. The best yield of AgNPs forming was obtained in pH 12.5 at 80 ºC in 20 min. TEM analysis confirmed the formation of spherical AgNPs with a size of 50 nm, at the 1% wt. loading of Preyssler. This easily prepared PC/AgNPs was successfully employed as an efficient, green, and reusable catalyst in the synthesis of a wide range of 2-amino-4 H -pyran and functionalized spirochromene derivatives via a one-pot, multicomponent reaction. The chief merits realized for this protocol were the utilization of commercially available or easily accessible starting materials, operational simplicity, facile work-up procedure, obtaining of high to excellent yields of the products and being done under green conditions. The catalyst could be easily separated from the reaction mixture and reused several times without observing any appreciable loss in its efficiency.

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Section: Resultsmentioning

confidence: 83%

Silver nanoparticles-decorated Preyssler functionalized cellulose biocomposite as a novel and efficient catalyst for the synthesis of 2-amino-4H-pyrans and spirochromenes

Saneinezhad

Mohammadi

Zadsirjan

et al. 2020

Sci Rep

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“…The catalytic strength of our specific catalyst (biochar/Fe 3 O 4 /PVIm/Ag) is compared with the recently detailed MCRs including acenaphthoquinone, malononitrile, and dimethyl ketone to use 2′-amino-tetrahydro-2 H -spiro[acenaphthylen-1,4′-chromeno]-3′-carbonitrile ( 14a ) and different catalysts, such as CaCl 2 57 , Fe 3 O 4 @Cs-CsO 3 H 56 , Na 2 EDTA 58 , HAuCl 4 . 3H 2 O 59 , Meglumine 41 , Fe 2 O 3 60 , HEAA 61 , Cu(OAc) 2 .H 2 O 46 , Fe 3 O 4 @CS-SO 3 H NPs 62 , Amb-400Cl (IRA-400 Cl) 63 , C 4 (DABCO-SO 3 H) 2 .4Cl 64 , Carbon-SO 3 H 65 , 1-butyl-3-methylimidazolium hydroxide ([bmim][OH] 66 , DBU 67 , (SB-DBU)Cl 68 , PEG-Ni nanoparticles 69 , trisodium citrate dihydrate 70 , PC/AgNPs 35 and new catalyst biochar/Fe 3 O 4 /PVIm/Ag. It seems that our new catalyst is better than other catalysts in more items.…”

Section: Resultsmentioning

confidence: 99%

“…ref 1 CaCl 2 0.02 50 r.t. Ultrasonic 96 57 2 Fe 3 O 4 @Cs-SO 3 H 0.02 300 Reflux H 2 O/EtOH 98 56 3 Na 2 EDTA 0.01 10 70 °C Solvent-free 94 58 4 HAuCl 4 . 3H 2 O 0.05 30 70 °C PEG 400 96 59 5 Meglumine 0.05 20 r.t. H 2 O/EtOH 93 41 6 Fe 2 O 3 0.02 240 90 °C Solvent-free 84 60 7 HEAA 0.02 60 90 °C H 2 O 92 61 …”

Section: Resultsmentioning

confidence: 99%

The preparation of polyvinyl imidazole-functionalized magnetic biochar decorated by silver nanoparticles as an efficient catalyst for the synthesis of spiro-2-Amino-4H-pyran compounds

Mohammadi

Heravi

Saljooqi

et al. 2022

Sci Rep

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The silver nanoparticle was synthesized by developing poly (1-vinylimidazole) on the surface of magnetized biochar (the stem and roots of Spear Thistle) (biochar/Fe3O4/PVIm/Ag). This nanocomposite was characterized by Fourier-transformed infrared spectroscopy (FTIR), powder X-ray diffraction (XRD), vibrating sample magnetometer (VSM), scanning electron microscopy-energy dispersive X-ray spectroscopy (SEM–EDS), and transmission electron microscopy (TEM). The SEM and TEM images of the nanocatalyst, biochar/Fe3O4/PVIm/Ag-NPs, confirmed the observation of microscopic sheets of biochar. The catalytic activity of these Ag NPs was tested via multicomponent reaction plus reusing to successful formation of 2-amino-4H-pyran and functionalized spirochromen derivatives. The prepared nanocatalyst was easily separated by an external magnet and reused in repeating coupling reaction cycles four times without remarkable activity loss. The catalyst showed great efficiency and reusability, thus making it an ideal candidate for catalytic purposes in several organic transformations.

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“…Li and co-workers 118 disclosed an efficient SnCl 2 -mediated carbonyl allylation of allyl bromide (127) to aldehydes and ketones (126) in IL/water mixture (Scheme 45).…”

Section: Allylationmentioning

confidence: 99%

“…Guo et al 126 described the ionic liquid 2-(hydroxyl)ethylammonium acetate (HEAA) catalyzed a three-component, one-pot condensation of quinone or ninhydrin (153), malononitrile/ethyl cyanoacetate (154) and 1,3-dicarbonyl compound/enol (155) in water to afford a spiropyran derivative (156). This method has advantages of mild reaction conditions, Su and co-workers 127 synthesized a series of 2,3-dihydroquinazolin-4(1H)-ones (160) in high to excellent yields through one-pot three-component cyclocondensation of isatoic anhydrides (157), ammonium acetate (158) and aldehydes (159) in IL/water solvent system without the use of any additional catalyst (Scheme 54).…”

Section: Three Component Coupling Reactionsmentioning

confidence: 99%

Ionic liquid/water mixture promoted organic transformations

et al. 2015

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Ionic liquid catalyzed one-pot synthesis of spiropyran derivatives via three-component reaction in water

Cited by 9 publications

References 20 publications

Silver nanoparticles-decorated Preyssler functionalized cellulose biocomposite as a novel and efficient catalyst for the synthesis of 2-amino-4H-pyrans and spirochromenes

Silver nanoparticles-decorated Preyssler functionalized cellulose biocomposite as a novel and efficient catalyst for the synthesis of 2-amino-4H-pyrans and spirochromenes

The preparation of polyvinyl imidazole-functionalized magnetic biochar decorated by silver nanoparticles as an efficient catalyst for the synthesis of spiro-2-Amino-4H-pyran compounds

Ionic liquid/water mixture promoted organic transformations

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