A rapid, convenient and chemoselective synthesis of acylals from aldehydes catalyzed by reusable nano-ordered MCM-41-SO3H

Tourani, Hesam; Naimi-Jamal, Mohammad Reza; Dekamin, Mohammad G.; Amirnejad, Meysam

doi:10.1016/j.crci.2012.06.014

Cited by 11 publications

(3 citation statements)

References 37 publications

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“…The MCM-41-SO 3 H was prepared according to our previous reports 57 , 59 , 60 and characterized by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), and Brunauer–Emmett–Teller analysis (BET). The FTIR spectrum of the catalyst has been shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones mediated by a nano-ordered reusable catalyst

Fathi¹,

Naimi-Jamal²,

Dekamin³

et al. 2021

Sci Rep

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A library of new spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-trione derivatives has been prepared in an efficient, one-pot pseudo four-component method mediated by a reusable heterogeneous nano-ordered mesoporous SO3H functionalized-silica (MCM-41-SO3H) catalyst. Excellent yields, short reaction times, as well as convenient non-chromatographic purification of the products and environmental benefits such as green and metal-free conditions constitute the main advantages of the developed synthetic methodology. The obtained fused indole-indenone dyes would be of interest to pharmaceutical and medicinal chemistry. Furthermore, due to their sensitivity to pH changes, they could be used as novel pH indicators.

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Section: Resultsmentioning

confidence: 99%

A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones mediated by a nano-ordered reusable catalyst

Fathi¹,

Naimi-Jamal²,

Dekamin³

et al. 2021

Sci Rep

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“…The possibility of achieving chemical reactions between the reactants without the need of any solvent is the most important aspect of this method, which is completely compatible with the green chemistry principles. Previously, we have reported a rapid, convenient and chemo‐selective method for protection of aldehydes as acylals catalyzed by reusable nano‐ordered mesoporous MCM‐41‐SO 3 H as a recoverable Bronsted acid catalyst . The effectiveness of the ball‐milling technique in preparation of Cu 2 (BDC) 2 (DABCO) NPs has been also reported by our group and its catalytic activity on preparation of carbamates has been investigated, recently .…”

Section: Introductionmentioning

confidence: 92%

Activity of M₂(BDC)₂(DABCO) (M= Co, Ni, Cu and Zn) Metal‐Organic Frameworks Prepared via Ball‐Milling Solvent‐Free Method in Acylation of Alcohols, Amines and Aldehydes

2018

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Metal-organic frameworks (MOFs) M 2 (BDC) 2 (DABCO), (M=Co, Ni, Cu and Zn, BDC = 1,4-benzenedicarboxylic acid, and DABCO = 1,4-diazabicyclo[2.2.2]octane) have been prepared via a simple and effective strategy by the ball-milling method, with no use of a solvent at room temperature. This method provides a facile, green, solvent-free and low-cost strategy for the preparation of Co, Ni, Cu and Zn based M 2 (BDC) 2 (DABCO) nanoporous particles (NPs) with square lattice structures. The structure and morphology of the MOFs were characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD) and scanning electron microscopy (SEM). The catalytic activity of the prepared MOFs was investigated in the acylation reaction of alcohols, amines and aldehydes with acetic anhydride in solvent-free method. The Lewis acid activity of the as-synthesized MOFs was drastically enhanced by microwave irradiation.

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“…On the other hand, the use of heterogeneous catalysts has been widely studied because they are easy to remove from the reaction media by simple filtration after completion of the reaction and in general, they are reusable without appreciable loss of their catalytic activity [37,38].…”

Section: Introductionmentioning

confidence: 99%

Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

et al. 2015

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4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H 14 P 5 NaW 30 O 110 ) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 °C, in a short reaction time (2 h). Under these conditions, very good yields (11 examples: 61 %-90 %), free of secondary products, were obtained. The catalyst is recyclable, nontoxic, neither air nor moisture sensitive, and easy to handle. The described methodology is a clean and useful alternative to synthesize oxygenated heterocycles based on a coumarin skeleton.

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A rapid, convenient and chemoselective synthesis of acylals from aldehydes catalyzed by reusable nano-ordered MCM-41-SO3H

Cited by 11 publications

References 37 publications

A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones mediated by a nano-ordered reusable catalyst

A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones mediated by a nano-ordered reusable catalyst

Activity of M₂(BDC)₂(DABCO) (M= Co, Ni, Cu and Zn) Metal‐Organic Frameworks Prepared via Ball‐Milling Solvent‐Free Method in Acylation of Alcohols, Amines and Aldehydes

Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

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A rapid, convenient and chemoselective synthesis of acylals from aldehydes catalyzed by reusable nano-ordered MCM-41-SO3H

Cited by 11 publications

References 37 publications

A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones mediated by a nano-ordered reusable catalyst

A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones mediated by a nano-ordered reusable catalyst

Activity of M2(BDC)2(DABCO) (M= Co, Ni, Cu and Zn) Metal‐Organic Frameworks Prepared via Ball‐Milling Solvent‐Free Method in Acylation of Alcohols, Amines and Aldehydes

Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

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Activity of M₂(BDC)₂(DABCO) (M= Co, Ni, Cu and Zn) Metal‐Organic Frameworks Prepared via Ball‐Milling Solvent‐Free Method in Acylation of Alcohols, Amines and Aldehydes