Highly effective synthesis of 1-thioamidoalkyl-2-naphthols and tetrahydropyridines using a nanostructured silica-based catalyst under mild conditions

2020 ◽  
Vol 23 ◽  
Author(s):  
Navid Irannejad-Gheshlaghchaei ◽  
Seyed Sajad Sajadikhah
Keyword(s):  
Solvent Free ◽  
One Pot ◽  
Mild Conditions ◽  
Solvent Free Conditions ◽  
Highly Effective ◽  
Effective Synthesis ◽  
The One ◽  
Yield Time ◽  
High Yields ◽  
Nanostructured Silica

Aim and Objective: Nano-2-[N',N'-dimethyl-N'-(silica-n-propyl)ethanaminium chloride]-N,N-dimethylaminium bisulfate (nano-[DSPECDA][HSO4]) was used as a highly effective and heterogeneous silica-based nanostructured catalyst for the synthesis of 1-thioamidoalkyl-2-naphthols and substituted tetrahydropyridines. Material and Methods: The expected products were prepared in mild conditions. In this work, three novel 1- thioamidoalkyl-2-naphthols and two new tetrahydropyridine derivatives were synthesized and characterized by IR, 1H and 13C NMR and Mass spectroscopy. Results: One-pot multi-component condensation of 2-naphthol with arylaldehydes and thioacetamide catalyzed by nano- [DSPECDA][HSO4] under green, mild and solvent-free conditions led to 1-thioamidoalkyl-2-naphthols in high yields. The nanocatalyst was also used for the preparation of functionalized tetrahydropyridines by the one-pot multi-component reaction of anilines, arylaldehydes and ethylacetoacetate under solvent-free and mild conditions. Conclusion: The reactions results are better compared to the literature in terms of one or more of these factors: yield, time, and the reaction media. All the products were purified by recrystallization from EtOH, and without column chromatography, which is good agreement with the green chemistry protocols.

A highly efficient and green approach for the synthesis of pyrimido[4,5-b]quinolines using N,N-diethyl-N-sulfoethanaminium chloride

2021 ◽  
Vol 76 (2) ◽  
pp. 85-90
Author(s):  
Abdolkarim Zare ◽  
Manije Dianat
Keyword(s):  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Catalyst Amount ◽  
Green Protocol ◽  
Highly Efficient ◽  
Green Approach ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

Abstract A highly efficient and green protocol for the synthesis of pyrimido[4,5-b]quinolines has been described. The one-pot multicomponent reaction of dimedone with arylaldehydes and 6-amino-1,3-dimethyluracil in the presence of N,N-diethyl-N-sulfoethanaminium chloride ([Et3N–SO3H][Cl]) as an ionic liquid (IL) catalyst under solvent-free conditions afforded the mentioned compounds in high yields and short reaction times. Our protocol is superior to many of the reported protocols in terms of two or more of these factors: the reaction times, yields, conditions (solvent-free versus usage of organic solvents), temperature and catalyst amount.

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

scholarly journals ZnO Nanoparticles: A Highly Effective and Readily Recyclable Catalyst for the One-Pot Synthesis of 1,8-dioxo-decahydroacridine and 1,8-dioxooctahydro-xanthene Derivatives

2017 ◽  
Vol 57 (1) ◽  
Author(s):  
Javad Safaei-Ghomi ◽  
Mohammad Ali Ghasemzadeh ◽  
Safura Zahedi
Keyword(s):  
Zno Nanoparticles ◽  
Environmentally Friendly ◽  
Recyclable Catalyst ◽  
Solvent Free ◽  
One Pot ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
Xanthene Derivatives ◽  
Highly Effective ◽  
The One

ZnO nanoparticles as a worthwhile and recyclable catalyst have been used for the one-pot synthesis of 1,8-dioxo-decahydroacridines and 1,8-dioxooctahydro-xanthenes via multi-component reactions under solvent-free conditions. The presented method is mild, environmentally friendly, inexpensive and highly effective to give the products in good to excellent yields.

scholarly journals Nano-Fe3O4@walnut shell/Cu(ii) as a highly effective environmentally friendly catalyst for the one-pot pseudo three-component synthesis of 1,3-oxazine derivatives under solvent-free conditions

RSC Advances ◽  
2020 ◽  
Vol 10 (53) ◽  
pp. 31874-31880
Author(s):  
Arefeh Dehghani Tafti ◽  
Bi Bi Fatemeh Mirjalili
Keyword(s):  
Alkaline Medium ◽  
Environmentally Friendly ◽  
Solvent Free ◽  
Walnut Shell ◽  
One Pot ◽  
Nano Catalyst ◽  
Solvent Free Conditions ◽  
Highly Effective ◽  
Nano Fe3o4 ◽  
The One

Fe3O4@walnut shell/Cu(ii) as an eco-friendly bio-based magnetic nano-catalyst was prepared by adding CuCl2 to Fe3O4@walnut shell in alkaline medium.

TiO2–SiO2 nanocomposite as a highly efficient catalyst for the solvent-free cyclocondensation reaction of isatins, cyclohexanones, and urea

2019 ◽  
Vol 74 (7-8) ◽  
pp. 559-564
Author(s):  
Simin Janitabar-Darzi ◽  
Shahrzad Abdolmohammadi
Keyword(s):  
Present Method ◽  
High Efficiency ◽  
Solvent Free ◽  
High Catalytic Activity ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Cyclocondensation Reaction ◽  
The One ◽  
High Yields

AbstractA TiO2–SiO2 nanocomposite catalyzes the one-pot cyclocondensation reaction of 1H-indole-2,3-diones (isatins), 1,3-cyclohexanediones, and urea at T = 70°C under solvent-free conditions with high efficiency. The present method affords the corresponding spiro products in high yields and short reaction time. The unique features of the TiO2–SiO2 nanocomposite are high catalytic activity, ease of preparation, non-toxicity, low loading, and recyclability.

scholarly journals Al(NO3)3 · 9H2O: An Efficient Catalyst for the One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Both under Reflux or Solvent-Free Conditions

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Eskandar Kolvari ◽  
Maryam Mirzaeeyan
Keyword(s):  
Low Cost ◽  
Biginelli Reaction ◽  
Acid Catalyst ◽  
Solvent Free ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Environmentally Friendly Process

Al(NO3)3 · 9H2O efficiently catalyzes the three-component Biginelli reaction between an aldehyde, aβ-dicarbonyl compound, and urea or thiourea in refluxing ethanol and solvent-free (SF) conditions to afford the corresponding dihydropyrimidinones in high yields. The advantages of this method involve the easy procedure, the environmentally friendly process, and the low cost of the Lewis acid catalyst.

scholarly journals MIL-101(Cr), an Efficient Heterogeneous Catalyst for One Pot Synthesis of 2,4,5-tri Substituted Imidazoles under Solvent Free Conditions

Nanomaterials ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 845
Author(s):  
Faranak Manteghi ◽  
Fatemeh Zakeri ◽  
Owen James Guy ◽  
Zari Tehrani
Keyword(s):  
Heterogeneous Catalyst ◽  
Metal Organic Framework ◽  
Solvent Free ◽  
Proton Nuclear Magnetic Resonance ◽  
One Pot ◽  
Acceptable Result ◽  
Solvent Free Conditions ◽  
Metal Organic ◽  
The One ◽  
High Yields

A chromium-containing metal-organic framework (MOF), MIL-101 (Chromium(III) benzene-1,4-dicarboxylate), was used to catalyze the one pot, three component synthesis of some 2,4,5-trisubstituted imidazoles under solvent-free conditions. The advantages of using this heterogeneous catalyst include short reaction time, high yields, easy and quick isolation of catalyst and products, low amount of catalyst needed, and that the addition of solvent, salt, and additives are not needed. This catalyst is highly efficient and can be recovered at least 5 times with a slight loss of efficiency. The structure of the metal-organic frameworks (MOF) was confirmed by X-ray diffraction (XRD) and field emission scanning electron microscopy (FESEM). Fourier transform infrared spectroscopy (FTIR) and proton nuclear magnetic resonance (HNMR) were performed to confirm some of the synthesized products. Experimental data indicated that the optimum amount of catalyst was 5 mg for benzil (1 mmol), 4-chlorobenzaldehyde (1 mmol), and ammonium acetate (2.5 mmol), and the synthetic route to the various imidazoles is performed in 10 min by 95% yield, an acceptable result rivalling those of other catalysts.

A highly effective and mild protocol for the production of 1-thioamidoalkyl-2-naphthols using 1,3-disulfonic acid imidazolium trifluoroacetate as a dual-functional catalyst

2018 ◽  
Vol 73 (5) ◽  
pp. 289-293 ◽  
Author(s):  
Mostafa Karami ◽  
Abdolkarim Zare
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
Reaction Times ◽  
Solvent Free ◽  
Disulfonic Acid ◽  
One Pot ◽  
Mild Conditions ◽  
Dual Functional ◽  
Highly Effective ◽  
High Yields

AbstractA solvent-free protocol for the production of 1-thioamidoalkyl-2-naphthols via a one-pot multi-component reaction of arylaldehydes with 2-naphthol and thioacetamide using the ionic liquid 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) is described. Furthermore, a plausible and attractive mechanism based on the dual functionality of the catalyst is proposed. Because of the dual functionality of [Dsim][TFA] (possessing acidic and basic sites), it is found to be generally highly effective, affording the products in high yields and short reaction times under mild conditions. We claim that this is one of the best protocols for the synthesis of 1-thioamidoalkyl-2-naphthols (in terms of yield, temperature, conditions, and/or the reaction time).

scholarly journals Fe3o4 nanoparticles: A highly efficient and easily reusable catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions

2013 ◽  
Vol 78 (6) ◽  
pp. 769-779 ◽  
Author(s):  
Ali Ghasemzadeh ◽  
Javad Safaei-Ghomi ◽  
Safura Zahedi
Keyword(s):  
Fe3o4 Nanoparticles ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Xanthene Derivatives ◽  
The One ◽  
High Yields

Magnetically separable Fe3O4 nanoparticles supply environmentally friendly procedure for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene and 1,8-dioxo-octahydro-xanthene derivatives. These compounds were obtained in high yields and short reaction times by the reaction of dimedone and 2-naphthol with various aromatic aldehydes under solvent-free conditions. The catalyst coluld be easily recovered using an external magnet and reused for six cycles with almost consistent activity.

Study of the Catalytic Activity of Zr(HPO4)2 in the Synthesis of Hexahydroquinoline Derivatives under Solvent-free Conditions

2013 ◽  
Vol 68 (2) ◽  
pp. 195-200 ◽  
Author(s):  
Shahrzad Abdolmohammadi
Keyword(s):  
Catalytic Activity ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

2-Amino-7,7-dimethyl-5-oxo-1,4-diaryl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile derivatives were synthesized by the one-pot four-component reaction of aromatic aldehydes, malononitrile, dimedone and arylamines in the presence of Zr(HPO4)2·H2O (α-ZrP) as an effective and recyclable solid acid catalyst, in high yields.

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