A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions

Maleki, Behrooz; Barzegar, Shahram; Sepehr, Zeinalabedin; Kermanian, Mina; Tayebee, Reza

doi:10.1007/s13738-012-0092-5

Cited by 52 publications

(19 citation statements)

References 66 publications

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“…In continuation of our research to develop new and eco-friendly synthetic methodologies [36][37][38][39][40][41][42][43][44][45][46] , we herein present efficient and environmentally benign protocols for the synthesis of isobenzofuran-1(3H)-one derivatives by condensation of phthalaldehydic acid (2-carboxy benzaldehyde) with aryl ketones or 1,3-dicarbonyl compounds catalyzed by H 2 SO 4 -SiO 2 under solventfree conditions at 120 0 C (Scheme 1). To further explore the scope of this protocol, we decided to investigate the condensation reaction of phthalaldehydic acid (2-carboxy benzaldehyde) with another aryl ketones or 1,3-dicarbonyl compounds (Table 2).…”

Section: Resultsmentioning

confidence: 99%

One-Pot Synthesis of Isobenzofuran-1(3h)-Ones Using Sulfuric Acid Immobilized on Silica Under Solvent-Free Conditions and Survey of Third-Order Nonlinear Optical Properties

Maleki

Koushki

Baghayeri

et al. 2015

J. Chil. Chem. Soc.

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Solvent-free synthesis of isobenzofuran-1(3H)-ones have been described via reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl or cyclic ketones using sulfuric acid immobilized on silica (H 2 SO 4 -SiO 2 ) in excellent yields (70-88%). The catalyst can be recovered by simple filtration and reused. Also, some of these compounds has been studied the third-order nonlinear optical properties by laser Gaussian z-scan techniques.

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Section: Resultsmentioning

confidence: 99%

One-Pot Synthesis of Isobenzofuran-1(3h)-Ones Using Sulfuric Acid Immobilized on Silica Under Solvent-Free Conditions and Survey of Third-Order Nonlinear Optical Properties

Maleki

Koushki

Baghayeri

et al. 2015

J. Chil. Chem. Soc.

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“…Tandem reactions offer many opportunities to improve chemical transformations such as Lewis acid–base catalysis, hydrogenation reactions and alkene metathesis . MCRs are currently well‐established methods for the synthesis of heterocycles, natural products and polymers while Double and Triple Cascade Reactions are still a growing field of research. Knoevenagel condensation–Michael addition (Double Cascade Reactions) and Knoevenagel condensation–Michael addition–cyclization (Triple Cascade Reactions) Sequences have been widely studied and frequently applied to the synthesis of natural products and biologically active compounds .…”

Section: Introductionmentioning

confidence: 99%

Guanine‐La complex supported onto SBA‐15: A novel efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component Tandem Knoevenagel condensation–Michael addition–cyclization Reactions

Nikoorazm

Khanmoradi

Mohammadi

2020

Applied Organom Chemis

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In this work, we present a simple, environmentally‐friendly and economical route for the preparation of a novel lanthanum (III) organometallic complex immobilized onto a highly stable mesoporous silica SBA‐15 (La‐guanine@SBA‐15) using an inexpensive and simple method and available materials. This mesoporous heterogenized complex was comprehensively characterized using FT‐IR, XRD, EDS, ICP, MAP, SEM, TGA and BET techniques. The catalytic activity of this mesoporous material was studied in one‐pot multi‐component tandem Knoevenagel condensation–Michael addition–cyclization reactions in order to prepare a series of benzo [a] pyrano [2, 3‐c] phenazine and 4,4′‐(arylmethylene)‐bis‐(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ols) derivatives under green conditions. This catalyst exhibited highly recoverable and recyclable features in consecutive reaction runs. Besides, the products were obtained in high yields and short reaction times. In this sense, simple preparation of the catalyst from the commercially available materials, simple operation, high catalytic activity, short reaction times, high yields and the use of green reaction conditions in the mentioned organic synthesis are the most significant advantages of this protocol. In addition, this nanocatalyst was easily recovered, using simple filtration, and reused several times without significant loss of its catalytic efficiency. Moreover, the leaching, heterogeneity and stability of La‐guanine@SBA‐15 were studied by hot filtration test and ICP technique. Finally, stability of the catalyst after recycling was confirmed by SEM and FT‐IR techniques.

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“…p ‐Dodecylbenezenesulfonic acid (DBSA), Amberlyst‐15, SmCl 3 , poly(2‐acrylamido‐2‐methyl‐1‐propanesulfonic acid‐ co ‐acrylic acid) (poly(AMPS– co –AA)), graphene oxide–SO 3 H (GO–SO 3 H), [Et 3 NH][HSO 4 ], cerric ammonium nitrate (CAN) supported HY‐zeolite, Mg–Al hydrotalcite, Mg(BF 4 ) 2 in ionic liquid 1‐butyl‐3‐methyl imidazolium tetrafluoroborate ([bmim]BF 4 ), sulfated zirconia, L‐pyrrolidine‐2‐carboxylic acid sulfate (LPCAS), and furfural‐imine‐functionalized graphene oxide‐copper oxide ((Cu(II)‐Fur‐APTES/GO)) have been used as catalysts for this reaction. However many of the reported procedures need to relatively high temperature conditions or an additional energy (ultrasound or microwave) and are performed in toxic organic solvents. The synthesis of 1,8‐dioxo‐octahydroxanthenes from the reaction of aldehydes with dimedone at room temperature are relatively rare .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Catalytic Application of Poly(2‐acrylamido‐2‐methyl‐1‐propanesulfonic acid‐co‐acrylamide) Grafted on Graphene Oxide

et al. 2019

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Graphene oxide was grafted with poly(2-acrylamido-2-methyl-1-propanesulfonic acid-co-acrylamide) (GO-poly(AMPS-co-AM)) by free radical copolymerization of the corresponding monomers namely acrylamide (AM) and 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS). The benzoyl peroxide (BPO) was used as initiator. The GO-poly(AMPS-co-AM) was characterized by Fourier transform infrared spectroscopy (FT-IR), Raman spectroscopy, X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal analysis (DTA), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), UV-Vis and fluorescence spectroscopy, and elemental analysis. The GO-poly(AMPS-co-AM) exhibited the acidic site loading of 0.85 mmol g À 1 , the maximum degradation temperatures (T max ) of 212, 292, and 406°C, the char yield of 30% at 800°C, the limiting oxygen index (LOI) of 29.5, an estimated band gap of 4.7 eV, and the fluorescence emission bands of 722, 800, and 880 nm at the excitation wavelengths (λ max ) of 360, 400, and 440 nm, respectively. The GO-poly (AMPS-co-AM) was used as a reusable catalyst for the preparation of 1,8-dioxo-octahydroxanthenes through the condensation of an aldehyde with 5,5-dimethyl-1,3-cyclohexanedione (dimedone) in H 2 O/EtOH (1:1) as green solvents at room temperature.[a] Prof.

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A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions

Cited by 52 publications

References 66 publications

One-Pot Synthesis of Isobenzofuran-1(3h)-Ones Using Sulfuric Acid Immobilized on Silica Under Solvent-Free Conditions and Survey of Third-Order Nonlinear Optical Properties

One-Pot Synthesis of Isobenzofuran-1(3h)-Ones Using Sulfuric Acid Immobilized on Silica Under Solvent-Free Conditions and Survey of Third-Order Nonlinear Optical Properties

Guanine‐La complex supported onto SBA‐15: A novel efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component Tandem Knoevenagel condensation–Michael addition–cyclization Reactions

Synthesis and Catalytic Application of Poly(2‐acrylamido‐2‐methyl‐1‐propanesulfonic acid‐co‐acrylamide) Grafted on Graphene Oxide

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