Solvent-Free Preparation of 1,8-Dioxo-Octahydroxanthenes Employing Iron Oxide Nanomaterials

Rajabi, Fatemeh; Abdollahi, Mohammad; Diarjani, Elham Sadat; Osmolowsky, M. G.; Osmolovskaya, O. M.; Gómez-López, Paulette; Santiago, Alain R. Puente; Luque, Rafael

doi:10.3390/ma12152386

Cited by 20 publications

(6 citation statements)

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“… 30 In recent years, many catalysts utilized to catalyze the formation of heteroanthracene molecules have been widely reported. 31 − 34 However, need toxic solvents, metal loss pollutes water, harsh reaction conditions, the amount of catalyst used is enormous and cannot be recovered, and the low product yield persists. 35 − 37 35 − 37 In this work, affordable and industrially manufactured poly(aluminum chloride) and silica gel were utilized as catalysts, and heteroanthracene compounds were prepared using a one-pot process under mechanical grinding.…”

Section: Resultsmentioning

confidence: 99%

“…1,8-Dioxa-octahydroanthracene compounds have extremely high pharmacological activity and use value in the fields of dyes and photosensitive materials and are antibacterial and anti-inflammatory, so they are considered to be the most practical type of heterocyclic compounds . In recent years, many catalysts utilized to catalyze the formation of heteroanthracene molecules have been widely reported. − However, need toxic solvents, metal loss pollutes water, harsh reaction conditions, the amount of catalyst used is enormous and cannot be recovered, and the low product yield persists. − − In this work, affordable and industrially manufactured poly(aluminum chloride) and silica gel were utilized as catalysts, and heteroanthracene compounds were prepared using a one-pot process under mechanical grinding. The catalytic activity of different catalysts is shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

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Exploring the In Situ Formation Mechanism of Polymeric Aluminum Chloride–Silica Gel Composites under Mechanical Grinding Conditions: As a High-Performance Nanocatalyst for the Synthesis of Xanthene and Pyrimidinone Compounds

et al. 2022

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The use of mechanical ball milling to facilitate the synthesis of organic compounds has attracted intense interest from organic chemists. Herein, we report a new process for the preparation of xanthene and pyrimidinone compounds by a one-pot method using polymeric aluminum chloride (PAC), silica gel, and reaction raw materials under mechanical grinding conditions. During the grinding process, polymeric aluminum chloride and silica gel were reconstituted in situ to obtain a new composite catalyst (PAC–silica gel). This catalyst has good stability (six cycles) and wide applicability (22 substrates). The Al–O–Si active center formed by in situ grinding recombination was revealed to be the key to the effective catalytic performance of the PAC–silica gel composites by the comprehensive analysis of the catalytic materials before and after use. In addition, the mechanism of action of the catalyst was verified using density functional theory, and the synthetic pathway of the xanthene compound was reasonably speculated with the experimental data. Mechanical ball milling serves two purposes in this process: not only to induce the self-assembly of silica and PAC into new composites but also to act as a driving force for the catalytic reaction to take place. From a practical point of view, this “one-pot” catalytic method eliminates the need for a complex preparation process for catalytic materials. This is a successful example of the application of mechanochemistry in materials and organic synthesis, offering unlimited possibilities for the application of inorganic polymer materials in green synthesis and catalysis promoted by mechanochemistry.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Exploring the In Situ Formation Mechanism of Polymeric Aluminum Chloride–Silica Gel Composites under Mechanical Grinding Conditions: As a High-Performance Nanocatalyst for the Synthesis of Xanthene and Pyrimidinone Compounds

et al. 2022

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“…Supported catalysts have both homogeneous and heterogeneous catalytic benefits (Wan and Zhao, 2007;Muñoz-Batista et al, 2018;. Among the suitable supports, SBA-15 silicate has received considerable attention due to its desirable properties such as regular channel nanostructures, a pore diameter in the range of 2-30 nm, a high surface-to-volume ratio, suitable selectivity, high thermal and mechanical stability, and adjustable surface chemistry (Zhao et al, 1998;Fulvio et al, 2005;Ostovar et al, 2018;Rajabi et al, 2019). In addition, the ability to design, manipulate, and modify the surface of SBA-15 by organic and inorganic materials due to large amounts of surface hydroxyl groups, which is a key factor for its application in catalytic processes, has led to special attention to these porous structures (Feng et al, 2010;Bhuyan et al, 2015;Ostovar et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Pd Doped on TCH@SBA-15 Nanocomposites: Fabrication and Application as a New Organometallic Catalyst in the Three-Component Synthesis of N-Benzo-imidazo- or -thiazole-1,3-thiazolidinones

Kalhor

Dadras

2021

Front. Chem.

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In this study, Pd(II)/TCH@SBA-15 nanocomposites were synthesized by the grafting of 3-chloropropyltriethoxysilane and thiocarbohydrazide on SBA-15 and subsequent deposition of palladium acetates through the ligand–metal coordination method. The structure and morphology of this nanoporous nanocomposite was thoroughly identified by Fourier transform infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, thermogravimetric analysis, atomic absorption spectroscopy, and Brunauer–Emmett–Teller instrumental analyses. Furthermore, the catalytic activity of this nanocomposite was investigated in the three-component synthesis of 3-benzimidazolyl or benzothiazoleyl-1,3-thiazolidin-4-ones via a reaction of 2-aminobenzimidazole or 2-aminobenzothiazole, aromatic aldehydes, and thioglycolic acid in an acetone–H2O mixture under green conditions. The Pd/TCH@SBA-15 nanocatalyst is demonstrated to exhibit a high catalyzing activity in the three-component reaction of the synthesis of N-heterocyclic thiazolidinones with good to excellent yields. One of the advantages of the suggested method is the direct application of the thiocarbohydrazide ligand to stabilize Pd nanoparticles through formation of a stable ring complex without creating an additional Schiff base step. Moreover, this organometallic nanocatalyst can be recycled several times with no notable leaching or loss of performance.

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“…Condensation of aldehydes, β-naphthol, and cyclic 1,3-dicarbonyl compounds is the simplest method for the synthesis of tetrahydrobenzoxanthene-11-ones. So far, many catalysts were used for synthesizing various xanthene derivatives such as nanocatalysts, [26][27][28][29][30][31] acid catalysts, [32,33] ionic liquids, [34,35] organocatalysts, [36,37] polymeric catalysts, [38] and natural catalysts. [39] However, such types of catalysts possessed some disadvantages like prolonged reaction time, toxic organic solvents, metal-based catalysts, sluggish reaction and low product yield, harsh reaction conditions, use of the excess quantity of catalysts, and difficult recovery and reusability of the catalyst.…”

Section: Introductionmentioning

confidence: 99%

Novel Carboxylic Acid Functionalized Dendronized Polymer: A Homogeneous, Reusable Metal Free Acid Catalyst for the Synthesis of Symmetric and Unsymmetric Xanthene Derivatives

et al. 2021

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In the present study, carboxylic acid‐functionalized tris(hydroxymethyl)propane initiated polyepichlorohydrin cored dendronized polymer (TMP‐PECH‐COOH) was successfully synthesized. Successful incorporation of carboxylic acid functionality was evidenced by Fourier transform infrared spectroscopy (FT‐IR), thermogravimetric analysis (TG/DTG), and NMR spectroscopy (1H NMR). Thermodynamic properties such as thermal energy, enthalpy, and Gibb's free energy as well as global reactivity descriptors such as chemical potential, chemical hardness, and electrophilicity index of the TMP‐PECH‐COOH dendronized polymer were investigated using Gaussian 09 program employing the hybrid density functional B3LYP method and 6‐31G basis set. The synthesized dendronized polymer (TMP‐PECH‐COOH) could act as a metal‐free acid catalyst for catalyzing the reactions for the synthesis of 1,8‐dioxooctahydroxanthenes and tetrahydrobenzoxanthene‐11‐ones under mild reaction conditions in an aqueous medium. The catalyst could be reused at least six times making the present procedure facile, practical, and sustainable. In addition, the efficiency of the present catalyst was compared with some previous reports.

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Solvent-Free Preparation of 1,8-Dioxo-Octahydroxanthenes Employing Iron Oxide Nanomaterials

Cited by 20 publications

References 50 publications

Exploring the In Situ Formation Mechanism of Polymeric Aluminum Chloride–Silica Gel Composites under Mechanical Grinding Conditions: As a High-Performance Nanocatalyst for the Synthesis of Xanthene and Pyrimidinone Compounds

Exploring the In Situ Formation Mechanism of Polymeric Aluminum Chloride–Silica Gel Composites under Mechanical Grinding Conditions: As a High-Performance Nanocatalyst for the Synthesis of Xanthene and Pyrimidinone Compounds

Pd Doped on TCH@SBA-15 Nanocomposites: Fabrication and Application as a New Organometallic Catalyst in the Three-Component Synthesis of N-Benzo-imidazo- or -thiazole-1,3-thiazolidinones

Novel Carboxylic Acid Functionalized Dendronized Polymer: A Homogeneous, Reusable Metal Free Acid Catalyst for the Synthesis of Symmetric and Unsymmetric Xanthene Derivatives

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