Nano titania-supported sulfonic acid (n-TSA) as an efficient, inexpensive, and reusable catalyst for one-pot synthesis of 1, 8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives

Amoozadeh, Ali; Hosseininya, Seyedeh Fatemeh; Rahmani, Shima

doi:10.1007/s11164-017-3148-4

Cited by 30 publications

(6 citation statements)

References 46 publications

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“…Amoozadeh and co‐workers [ 72 ] devised an efficient and solvent‐free methodology for tetrahydrobenzopyrans from diketones, different aromatic aldehydes, and malononitrile using nanotitania supported sulfonic acid (n‐TSA) (Scheme 25). The designed protocol gave good yield of products irrespective of the nature of substitution on aromatic aldehydes.…”

Section: Different Synthetic Methodologies For Substituted Pyran Deri...mentioning

confidence: 99%

An overview of recent advances in the catalytic synthesis of substituted pyrans

Agarwal¹,

Sethiya²,

Soni³

et al. 2022

Applied Organom Chemis

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Substituted pyrans (4H‐Chromenes) are the most significant structural scaffolds in synthetic and medicinal chemistry. They are found in an array of natural products, medicines, and phytochemical compounds, bearing an explicit of pharmacological activities. The structural importance of substituted pyrans has elicited a huge upsurge in the field of synthesis and biology. Different synthetic approaches of 4H‐chromene scaffolds have been discussed systematically to emphasize their significance in the scientific world. The present article summarizes the different synthetic strategies of substituted pyran derivatives via acid‐base catalysis, ionic liquids, nanomaterials, deep eutectic solvents, bio‐based, visible light, metal catalyzed, and so forth developed in the last decade. Moreover, this article will definitely contribute to the scientific world for developing synthetically and biologically important pyran analogs.

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Section: Different Synthetic Methodologies For Substituted Pyran Deri...mentioning

confidence: 99%

An overview of recent advances in the catalytic synthesis of substituted pyrans

Agarwal¹,

Sethiya²,

Soni³

et al. 2022

Applied Organom Chemis

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“…To the best of our knowledge, the interaction of -dicarbonyl compounds with phenyl-allylidene-malononitriles leads to the formation of xanthene, benzo [b]pyran and pyridine derivatives (Bardasov et al, 2014;Amoozadeh et al, 2018). Interestingly, we discovered that in case of the reaction of one equivalent of phenyl-allylidene-malononitrile with two equivalents of benzoylacetone at room temperature, a substituted cyclohexane derivative was the product.…”

Section: Chemical Contextmentioning

confidence: 98%

Crystal structure and Hirshfeld surface analysis of 3-benzoyl-6-(1,3-dioxo-1-phenylbutan-2-yl)-2-hydroxy-2-methyl-4-phenylcyclohexane-1,1-dicarbonitrile

Naghiyev¹,

Хрусталев²,

Dobrokhotova³

et al. 2022

Acta Cryst E

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The central cyclohexane ring of the title compound, C32H28N2O4, adopts a chair conformation, with puckering parameters Q T = 0.618 (2) Å, θ = 176.72 (19)° and φ = 290 (3)°. In the crystal, molecules are linked by O—H...O, C—H...O and C—H...N hydrogen bonds, forming layers parallel to (100). These layers are linked by weak C—H...π interactions and van der Waals forces. A Hirshfeld surface analysis indicates that the contributions from the most prevalent interactions are H...H (41.2% contribution), C...H/H...C (20.3%), O...H/H...O (17.8%) and N...H/H...N (10.6%).

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“… Entry Catalyst Solvent catalyst loading Temp. (°C) Yield (%) References 1 Ag@Sep-N–CH H 2 O:EtOH 0.03 g 50 95 This work 2 Nano-ZnO – 10 mol% 100 Trace 21 3 Fe 2 (SO 4 ) 3 .7H 2 O – 10 mol% 120 86 35 4 Fe 3 O 4 @SiO 2 –SO 3 H – 0.05 g 110 97 22 5 Silica-bonded S-sulfonic acid (SBSSA) EtOH 0.03 g Reflux 98 23 6 Nano-NiO – 10 mol% 100 Trace 21 7 Barium Perchlorate EtOH 15 mol% Reflux 95 36 8 Nano titania-supported sulfonic acid (n-TSA) ...…”

Section: Comparison Of the Catalytic Activity Of Ag@sep-n–ch With Othmentioning

confidence: 98%

Bio-assisted synthesized Ag(0) nanoparticles stabilized on hybrid of sepiolite and chitin: efficient catalytic system for xanthene synthesis

Kahangi

Mehrdad

Heravi

et al. 2020

Sci Rep

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In this work, with the use of two natural compounds, chitin and sepiolite clay, a novel covalent hybrid is fabricated and applied as a support for the stabilization of silver nanoparticles with the aid of Kombucha extract as a natural reducing agent. The resultant catalytic system, Ag@Sep-N–CH, was characterized via XRD, TEM, FTIR, ICP, SEM, TGA, UV–Vis and BET. It was found that fine Ag(0) nanoparticles with mean diameter of 6.1 ± 1.8 nm were formed on the support and the specific surface area of the catalyst was 130 m2 g−1. The study of the catalytic performance of Ag@Sep-N–CH for catalyzing synthesis of xanthenes in aqueous media under mild reaction condition confirmed that Ag@Sep-N–CH exhibited high catalytic activity and could promote the reaction of various substrates to furnish the corresponding products in high yields. Moreover, the contribution of both chitin and sepiolite to the catalysis has been affirmed. It was found that hybridization of these two components led to synergistic effects and consequently improved the observed catalytic activity. Notably, the catalyst was recyclable up to several reaction runs.

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Nano titania-supported sulfonic acid (n-TSA) as an efficient, inexpensive, and reusable catalyst for one-pot synthesis of 1, 8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives

Cited by 30 publications

References 46 publications

An overview of recent advances in the catalytic synthesis of substituted pyrans

An overview of recent advances in the catalytic synthesis of substituted pyrans

Crystal structure and Hirshfeld surface analysis of 3-benzoyl-6-(1,3-dioxo-1-phenylbutan-2-yl)-2-hydroxy-2-methyl-4-phenylcyclohexane-1,1-dicarbonitrile

Bio-assisted synthesized Ag(0) nanoparticles stabilized on hybrid of sepiolite and chitin: efficient catalytic system for xanthene synthesis

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