- Design and characterization of nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a novel, heterogeneous and reusable catalyst for the condensation of arylaldehydes with β-naphthol and alkyl carbamates
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In this research, nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a new and efficient Br?nsted acidic ionic liquid supported on silica has been synthesized, and characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, thermogravimetric, differential thermal gravimetric, X-ray diffraction, and energy-dispersive X-ray spectroscopy spectra. The presented silica-supported ionic liquid has been applied as a highly effective, heterogeneous, easy regenerable, and reusable catalytic system for the solvent-free condensation of arylaldehydes with β-naphthol and alkyl carbamates leading to α-carbamatoalkyl-β-naphthols. Once the nanocatalyst was regenerated and reused, no significant loss of its activity was observed. Graphical Abstract: Design and characterization of nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a novel, heterogeneous and reusable catalyst for the condensation of arylaldehydes with β-naphthol and alkyl carbamates.[Figure not available: see fulltext.]
- Zare, Abdolkarim,Merajoddin, Maria,Moosavi-Zare, Ahmad Reza,Zarei, Mahmoud,Beyzavi, M. Hassan,Zolfigol, Mohammad Ali
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p. 2365 - 2378
(2016/03/16)
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- Preparation of methyl/benzyl(2-hydroxynaphthalen-1-yl)(aryl)methylcarbamate derivatives using magnesium hydrogen sulfate
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A new approach to the synthesis of methyl/benzyl(2-hydroxynaphthalen-1-yl) (aryl)methylcarbamate derivatives based on the reaction of aldehydes, 2-naphthol and methyl/benzyl carbamate, using a catalytic amount of magnesium hydrogen sulfate [Mg(HSO4/
- Ghashang, Majid
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p. 1357 - 1364
(2014/05/06)
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- Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media
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Trityl chloride (TrCl), efficiently catalyzes the one-pot multi-component condensation of β-naphthol with aromatic aldehydes and amides/thioamides/ carbamates such as acetamide, benzamide, nicotinamide, thioacetamide, and methylcarbamate under solvent-free and neutral conditions to afford 1-amido-alkyl-2-naphthols, 1-thioamido-alkyl-2-naphthols, and 1-carbamato-alkyl-2-naphthols in high yields and very short reaction times. Mechanistically, it is interesting that trityl chloride through the in situ generation of trityl carbocation with inherent instability is efficient as a reusable homogeneous organocatalyst in neutral media.
- Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Moosavi-Zare, Ahmad Reza,Abi, Fereshteh,Zare, Abdolkarim,Kaveh, Hamideh,Khakyzadeh, Vahid,Kazem-Rostami, Masoud,Parhami, Abolfath,Torabi-Monfared, Hossein
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p. 212 - 218
(2013/01/15)
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- Saccharin sulfonic acid (SASA) as a highly efficient catalyst for the condensation of 2-naphthol with arylaldehydes and amides (thioamides or alkyl carbamates) under green, mild, and solvent-free conditions
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Saccharin sulfonic acid (SaSA) is used as a highly efficient and recyclable catalyst for the one-pot multicomponent condensation of 2-naphthol with arylaldehydes and amides (thioamides or alkyl carbamates) under green, mild (70 °C), and solvent-free conditions. In this reaction, 1-amidoalkyl-2- naphthols, 1-thioamidoalkyl-2-naphthols, 1-carbamatoalkyl-2-naphthols, bis(1-amidoalkyl-2-naphthol)s, and bis(1-carbamatoalkyl-2-naphthol)s are produced in high to excellent yields and in relatively short reaction times. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Zare, Abdolkarim,Kaveh, Hamideh,Merajoddin, Maria,Moosavi-Zare, Ahmad Reza,Hasaninejad, Alireza,Zolfigol, Mohammad Ali
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p. 573 - 584
(2013/07/25)
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- Nanocrystalline TiO2-HClO4 catalyzed three-component preparation of derivatives of 1-amidoalkyl-2-naphthol, 1-carbamato-alkyl-2- naphthol, 1-(α-aminoalkyl)-2-naphthol, and 12-aryl-8,9,10,12- tetrahydrobenzo[a]-xanthen-11-one
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1-Amidoalkyl-2-naphthols, 1-carbamatoalkyl-2-naphthols, and 1-(α-aminoalkyl)-2-naphthols have been prepared by three-component reaction of 2-naphthol, aromatic aldehydes, and NH compounds, i.e. amides, carbamates, and secondary amines, respectively, in th
- Shaterian, Hamid Reza,Mohammadnia, Majid
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p. 4221 - 4237
(2013/11/19)
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- Triethylamine-bonded sulfonic acid ([Et3N-SO3H]Cl): A highly efficient and homogeneous catalyst for the condensation of 2-naphthol with arylaldehydes and amides (alkyl carbamates or thioamides)
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Ionic liquid triethylamine-bonded sulfonic acid ([Et3N-SO 3H]Cl, N,N-diethyl-N-sulfoethanammonium chloride) is utilized as a highly efficient, inexpensive and homogeneous catalyst to promote the following one-pot multi-component organic transformations under solvent-free conditions: (i) the condensation of 2-naphthol with arylaldehydes and amides leading to 1-amidoalkyl-2-naphthols, (ii) the reaction of 2- naphthol with aromatic aldehydes and alkyl carbamates to produce 1-carbamatoalkyl-2-naphthols, and (iii) the condensation between 2-naphthol, arylaldehydes and thioamides leading to 1-thioamidoalkyl-2- naphthols. High yields, short reaction times, efficiency, generality, clean process, simple methodology, low cost, easy work-up, ease of preparation of the catalyst, and environmentally benign conditions are some advantages of the protocols.
- Zare, Abdolkarim,Akbarzadeh, Shayesteh,Foroozani, Elmira,Kaveh, Hamideh,Moosavi-Zare, Ahmad Reza,Hasaninejad, Alireza,Mokhlesi, Mohammad,Beyzavi, Mohammad Hassan,Zolfigol, Mohammad Ali
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experimental part
p. 259 - 272
(2012/08/27)
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- Bronsted acidic ionic liquids as efficient catalysts for clean synthesis of carbamatoalkyl naphthols
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Under mild conditions and without any additional organic solvent, synthesis of carbamatoalkyl naphthols could be carried out in the present of two halogen-free Bronsted acidic ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate and N-(4-sulfonic acid)butylpyridinium hydrogen sulfate. A widerange of aromatic aldehydes easily undergo condensation with β-naphthol and methyl or benzyl carbamate to afford the desired products of good purity in excellent yields. The present methodology offers several advantages such as a simple procedure with an easy work-up, short reaction times, and excellent yields. The catalysts could be recycled and reused for several times without substantial reduction in their catalytic activities. Copyright
- Tavakoli-Hoseini, Niloofar,Heravi, Majid M.,Bamoharram, Fatemeh F.,Davoodnia, Abolghasem
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experimental part
p. 787 - 792
(2011/12/22)
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- Synthesis of new and novel N-protected 1-aminoalkyl-2-naphthol derivatives
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A series of three-component reactions has been carried out using HClO4-SiO2 as a versatile heterogeneous catalyst. A series of new and novel N-protected 1-aminoalkyl-2-naphthol derivatives have been prepared under thermal solvent-free reaction conditions.
- Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid
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experimental part
p. 2560 - 2574
(2009/12/04)
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- A three-component novel synthesis of 1-carbamato-alkyl-2-naphthol derivatives
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A new one-pot, efficient three-component condensation of benzaldehydes, 2-naphthol, and carbamates in the presence of silica supported sodium hydrogen sulfate as an effective heterogeneous catalyst for the synthesis of novel 1-carbamato-alkyl-2-naphthol d
- Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid
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p. 5804 - 5806
(2008/12/22)
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