- Graphene oxide supported dicationic ionic liquid: an efficient catalyst for the synthesis of 1-carbamatoalkyl-2-naphthols
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This article describes the synthesis, characterization, and catalytic application of graphene oxide (GO) supported imidazolium based dicationic ionic liquid (DIL@GO). The DIL@GO was successfully synthesized through stepwise functionalization of GO. The as prepared DIL@GO was characterized by different microscopic and spectroscopic techniques such as XRD, SEM, TEM, TGA, FT-IR, EDX and CHNS analysis. The catalytic efficiency of the DIL@GO was explored for the synthesis of 1-carbamatoalkyl-2-naphthol derivatives through condensation of aromatic aldehydes, alkyl carbamates and 2-naphthol. The influence of catalyst amount and reaction temperature is examined to optimize the performance of catalytic reactions. It is found that DIL@GO offers a highly efficient solvent-free reaction path for the synthesis of 1-carbamatoalkyl-2-naphthols. Based on this, a plausible mechanism for the conversion is proposed. Additionally, the catalyst showed good stability, facile separation and reusability up to five reaction cycles without significant loss of catalytic activity.
- Patel, Nipun,Katheriya, Deepak,Dadhania, Harsh,Dadhania, Abhishek
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p. 5595 - 5607
(2019/07/17)
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- Evaluation of catalytic activity of two newly prepared functionalized sulfonic acids ionic liquids in the synthesis of carbamatoalkyl naphthols under mild conditions
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Catalytic activity of two newly prepared functionalized sulfonic acids ionic liquids, [MPyrrSO3H]Cl (IL1) and [MMorSO3H]Cl (IL2), is studied in one-pot three-component synthesis of carbamatoalkyl naphthols by th
- Dehghan,Davoodnia,Bozorgmehr,Bamoharram
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p. 311 - 315
(2017/04/13)
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- 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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- Magnetically retrievable magnetite (Fe3O4) immobilized ionic liquid: An efficient catalyst for the preparation of 1-carbamatoalkyl-2-naphthols
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A magnetite (Fe3O4) supported -SO3H functionalized benzimidazolium based ionic liquid has been synthesized via covalent grafting of benzimidazole on a (3-chloropropyl)triethoxysilane functionalized magnetic nanoparticle followed by quaternization reaction with 1,4-butane sultone. The obtained magnetic nanoparticle supported ionic liquid (IL@MNP) has been characterized by FT-IR, TGA, TEM, XRD, VSM, EDX and elemental analysis. The performance of the prepared catalyst was evaluated in the preparation of 1-carbamatoalkyl-2-naphthols. The magnetite supported catalyst showed excellent catalytic activity and the corresponding products were obtained in high yields in all the tested cases. The heterogeneous nature of the magnetite favoured easy recovery and recyclability of the catalyst through magnetic decantation making the protocol highly advantageous over conventional procedures.
- Dadhania, Harsh N.,Raval, Dipak K.,Dadhania, Abhishek N.
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p. 4806 - 4812
(2015/10/05)
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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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- Copper chloride-catalyzed efficient three-component one-pot synthesis of carbamatoalkyl naphthols under solvent-free conditions
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A highly efficient synthesis of carbamatoalkyl naphthols by a one-pot three-component condensation of 2-naphthol, aldehydes, and methyl/ethyl/benzyl carbamates in the presence of copper chloride under thermal solvent-free conditions has been performed. The suitable solvent, amounts of raw materials and catalyst, and reaction temperature were investigated. Experimental results show that only 1 mol% catalyst was enough to induce the conversion. All new products were characterized by mp, IR, 1H NMR, 13C NMR and mass spectrum. A mechanism to rationalize the reaction was proposed.
- Song, Zhiguo,Liu, Lianli,Sun, Xiaohu,Cui, Yan
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p. 740 - 745
(2014/07/07)
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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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- Solvent-free one-pot synthesis of 1-carbamatoalkyl-2-naphthols by a tin tetrachloride catalyzed multicomponent reaction
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An efficient one-pot synthesis of 1-carbamatoalkyl-2-naphthols using tin tetrachloride as a catalyst for the three-component condensation reaction of 2-naphthol, aldehydes, and carbamates under thermal, solvent-free conditions is described. This new approach has advantages such as mild conditions, short reaction time, high yield, simple work-up, and an inexpensive catalyst. Graphical Abstract: [Figure not available: see fulltext.]
- Wang, Min,Wang, Qing L.,Zhao, Shuang,Wan, Xin
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p. 975 - 980
(2013/07/26)
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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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- A convenient three-component synthesis of carbamatoalkyl naphthols catalyzed by cerium ammonium nitrate
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A highly efficient synthesis of carbamatoalkyl naphthols has been performed by a one-pot threecomponent condensation of 2-naphthol, aldehydes, and methyl/ethyl/benzyl carbamates in the presence of cerium ammonium nitrate under solvent-free conditions at 70 °C. The solvent, optimal amounts of raw materials and catalyst, and reaction temperature are investigated. Experimental results show that only 0.1 mmol catalyst is enough to induce the conversion. Most reactions are performed within a short reaction time. The structures of all products were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analysis. A mechanism to rationalize the reaction has been proposed.
- Wang, Min,Liu, Yang,Song, Zhiguo,Zhao, Shuang
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p. 421 - 426
(2013/12/04)
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- Synthesis of 1-carbamatoalkyl-2-naphthols in Tween 20 aqueous micelles
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A facile and efficient procedure for the preparation of 1-carbamatoalkyl-2-naphthols by a one-pot multi-component reaction of 2-naphthol, aldehydes and carbamates is described. The procedure is carried out under neutral conditions at 75-80 °C in an aqueous medium catalysed by the non-ionic surfactant Tween A loading of 20. 5 wt% of the catalyst was optimal. After the reaction, the catalyst could be simply recovered and reused directly without any further treatment. Product yields were slightly decreased after six cycles. The effect of some common solvents other than water on the reaction was explored besides the water. The generality of this multi-component condensation reaction was evaluated with various aldehydes and carbamates under the optimised conditions.
- Yang, Jin-Ming,Jiang, Chen-Njing,Dong, Hao,Fang, Dong
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p. 279 - 281
(2013/07/27)
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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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- Sulfamic acid functionalised magnetic nanoparticles: An efficient solid acid for the multicomponent condensations
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Sulfamic acid-functionalised magnetic nanoparticles have been synthesised and used as efficient heterogeneous solid acid catalysts for the condensation of aromatic aldehydes with 2-naphthol and amides (or carbamates) via three-component reactions under solvent-free conditions at 80°C. Quantitative conversion of the reactants is achieved under mild conditions. Recovery of the catalyst is easily achieved by 'magnetic decantation'. The supported catalyst is reused four times without any significant degradation in catalytic activity.
- Yarahmadi, Hossein,Shaterian, Hamid Reza
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scheme or table
p. 52 - 55
(2012/03/27)
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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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- Preparation of methyl (2-hydroxynaphthalen-1-yl)(aryl)methyl/ benzylcarbamate derivatives using magnesium (II) 2,2,2-trifluoroacetate as an efficient catalyst
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Multi-component condensation reactions of aldehydes, 2-naphthol and methyl/benzyl carbamate have been done by using magnesium 2,2,2-trifluoroacetate [Mg(OOCCF3)2] as an efficient catalyst. This methodology results in the synthesis of a variety
- Shafiee, Mohammad Reza Mohammad,Moloudi, Raheleh,Ghashang, Majid
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p. 622 - 625,4
(2020/07/30)
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- Zwitterionic-type molten salt: An efficient mild organocatalyst for synthesis of 2-amidoalkyl and 2-carbamatoalkyl naphthols
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A green, general, and efficient method has been developed for the synthesis of 2-amidoalkyl and 2-carbamatoalkyl naphthol derivatives through a one-pot three-component condensation of 2-naphthol, aldehydes and amide or carbamates in the presence of zwitte
- Kundu, Dhiman,Majee, Adinath,Hajra, Alakananda
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scheme or table
p. 1157 - 1159
(2010/11/17)
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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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