- β-naphthol in glycerol: A versatile pair for efficient and convenient synthesis of aminonaphthols, naphtho-1,3-oxazines, and benzoxanthenes
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Three-component Betti reaction was carried out in the environmentally benign, inexpensive, non-toxic solvent glycerol. Even in the absence of a catalyst, the reaction went completion with an unprecedented high rate and the expected Betti bases were obtained in up to 91% yield. The reaction works well for representative cyclic, acyclic, aliphatic, and aromatic amines and aldehydes. A benzoxanthene was also prepared in 93% yield following the same methodology with 20 mol% methanesulfonic acid catalyst. Georg Thieme Verlag Stuttgart New York.
- Ganesan, Subramaniapillai Selva,Rajendran, Narendran,Sundarakumar, Sankahr Ilathur,Ganesan, Asaithampi,Pemiah, Brindha
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- Synthesis, growth, physicochemical properties and DFT calculations of 2-naphthol substituted Mannich base 1-(morpholino(phenyl) methyl) naphthalen-2-ol: A non linear optical single crystal
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2-Naphthol substituted Mannich base 1-morpholino(phenyl)methyl)naphthalen-2-ol (MPMN), a potential NLO active organic single crystal was developed using acetonitrile as a solvent by slow evaporation method. The experimental and theoretical analysis made t
- Dennis Raj,Jeeva,Shankar,Venkatesa Prabhu,Vimalan,Vetha Potheher
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Read Online
- Facile synthesis of aminoalkyl naphthols and single crystal X-ray, computational studies on 1-[morpholino(thiophen-2-yl)methyl]naphthalen-2-ol
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An efficient, eco-friendly protocol is developed for the synthesis of 1- (α-aminoalkyl)-2-naphthol derivatives via one-pot three-component reaction of 2-naphthol, aromatic aldehydes and piperidine or morpholine in the presence of Amberlite IRA-400 Cl resi
- Harichandran, G.,Muthu, S.,Surya, C. P.
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- Synthesis of 1-aminoalkyl-2-naphthols derivatives using an engineered copper-based nanomagnetic catalyst (Fe3O4@CQD@Si (OEt)(CH2)3NH@CC@N3@phenylacetylene@Cu)
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In the present study, a molecular level engineered-based method was used to synthesis a copper-based nanomagnetic catalyst (Fe3O4@CQD@Si (OEt)(CH2)3NH@CC@N3@phenylacetylene@Cu). The as-synthesized cat
- Akbarpour, Tahereh,Khazaei, Ardeshir,Sarmasti, Negin,Yousefi Seyf, Jaber
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- An efficient, multicomponent synthesis of aminoalkylnaphthols via Betti reaction using ZSM-5 as a recoverable and reusable catalyst
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The design and application of environmentally friendly catalysts to reduce the number of toxic wastes are critical for improving the chemical synthetic protocols. A simple, mild, efficient, and eco-friendly method was developed for the synthesis of a seri
- Keri, Rangappa S.,Patil, Mahadeo,Budagumpi, Srinivasa,Sasidhar, Balappa S.
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- Design and identification of nano-Mg-[4-methoxy phenyl-salicylaldimine–methyl-pyranopyrzole] Cl2 and its catalytic application on the preparation of 1-(α-aminoalkyl)-2-naphthols
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Nano-Mg- [4-methoxy phenylsalicylaldiminemethylpyranopyrazole]Cl2 (nano-[Mg-4MSMP]Cl2) as a nano-Schiff base complex was prepared and fully characterized using some various techniques including fourier transform infrared spectroscopy
- Goudarziafshar, Hamid,Moosavi-Zare, Ahmad Reza,Hasani, Jafar
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- Cu/Ag mediated peroxide-free synthesis of benzoylated naphthol derivatives
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A peroxide-free methodology was developed for the synthesis of benzoylated naphthol/phenol derivatives through oxidative deamination reaction performed under aerobic reaction conditions. A synergistic combination of Cu(OTf)2 and Ag2O was used to convert the aminonaphthols and aminophenols to the corresponding benzoylated derivatives. The definite role of atmospheric oxygen to assist the reaction was proved by performing the reaction in the argon atmosphere.
- Prasanna Kumari, Subramaniyan,Suresh, Pavithira,Muthukumar, Vijayashree,Selva Ganesan, Subramaniapillai
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supporting information
(2020/10/13)
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- Synthesis of Betti base derivatives catalyzed by nano-CuO-ionic liquid and experimental and quantum chemical studies on corrosion inhibition performance of them
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In this research, for the first time, aminonaphthol derivatives were introduced as efficient corrosion inhibitors. A linear polarization method was employed to investigate the corrosion inhibitory effect of the synthesized aminonaphthols at a concentratio
- Teimuri-Mofrad, Reza,Ahadzadeh, Iraj,Gholamhosseini-Nazari, Mahdi,Esmati, Somayeh,Shahrisa, Aziz
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p. 2913 - 2927
(2018/02/06)
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- Microwave-assisted nanocatalysis: A CuO NPs/rGO composite as an efficient and recyclable catalyst for the Petasis-borono-Mannich reaction
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A CuO NP decorated reduced graphene oxide (CuO NPs/rGO) composite was synthesized and characterized using various analytical techniques viz. XRD, TEM, SEM, UV-Vis, FT-IR, EDX, XPS and CV. The activity of the catalyst was probed for the Petasis-Borono-Mann
- Dandia, Anshu,Bansal, Sarika,Sharma, Ruchi,Rathore, Kuldeep S.,Parewa, Vijay
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p. 30280 - 30288
(2018/09/11)
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- Multicomponent reaction in deep eutectic solvent for synthesis of substituted 1-aminoalkyl-2-naphthols
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One-pot multicomponent synthesis of Betti bases (aminoalkyl naphthols) from aldehydes, β-naphthol, and secondary amines in deep eutectic solvent (DES) based on urea and choline chloride has been developed. A broad range of aminoalkyl naphthols can be obta
- Azizi, Najmedin,Edrisi, Mahtab
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p. 379 - 385
(2017/01/14)
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- An efficient and green method for the synthesis of Betti base employing nano-SiO2–H3BO3 as a novel recyclable heterogeneous catalyst
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Abstract: In this research, nano-SiO2–H3BO3 is introduced as a novel environmentally benign and recyclable heterogeneous catalyst for the synthesis of aminonaphthols under solvent-free conditions without an additional co-catalyst or additive in air. This synthesis method offers several advantages, such as a green and eco-friendly protocol, operational simplicity, mild reaction conditions, short reaction times, higher yields and easy work-up procedures. The work-up of these very clean reactions involves only recrystallization of the product from ethanol and recovery of the catalyst by filtration. The catalyst can be reused several times without losing activity.
- Teimuri-Mofrad, Reza,Gholamhosseini-Nazari, Mahdi,Esmati, Somayeh,Shahrisa, Aziz
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p. 6845 - 6861
(2017/10/06)
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- Aluminatesulfonic acid: Novel and recyclable nanocatalyst for efficient synthesis of aminoalkyl naphthols and amidoalkyl naphthols
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In this study, an efficient, mild, and eco-friendly procedure is developed for the preparation of 1-amidoalkyl-2-naphthols and Betti bases from one-pot three-component condensation of aldehydes, 2-naphthol, and nitrogen sources (amides for amidoalkyl naphthols and amine for Betti bases) in the presence of aluminatesulfonic acid nanoparticles (ASA NPs) as recoverable catalyst under solvent-free conditions. ASA NPs were prepared by a simple reaction of net chlorosulfonic acid and sodium aluminate in high purity. ASA NPs were characterized by Fourier transform IR, X-ray powder diffraction, transmission electron microscopy, energy-dispersive X-ray, thermal gravimetric analysis, and UV diffusion/reflectance techniques. On the basis of the thermal gravimetric analysis and some activation parameters evaluated from decomposition thermal steps using Coats–Redfern model, the catalyst showed high thermal stability. High yields, short reaction time, easy workup, inexpensive, and reusability of the catalyst are advantages of this method.
- Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Taei, Mahbube
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p. 986 - 994
(2016/08/08)
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- Metal-free new synthesis of 1,3-naphthoxazines via intramolecular cross dehydrogenative-coupling reaction of 1-(α-aminoalkyl)-2-naphthols using hypervalent iodine(III) reagent
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A series of 1-(α-aminoalkyl)-2-naphthols were synthesized via three-component Betti reaction of β-naphthol, aldehyde, and cyclic secondary amine under reflux conditions. The subsequent reactions of 1-(α-aminoalkyl)-2-naphthols with (diacetoxyiodo)benzene
- Waghmode, Nitin A.,Kalbandhe, Amit H.,Thorat, Prerana B.,Karade, Nandkishor N.
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supporting information
p. 680 - 683
(2016/01/26)
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- Diastereoselective α-C-H functionalization of aliphatic N-heterocycles: An efficient route to ring fused oxazines
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A novel method for direct C-H functionalization of saturated N-heterocycles allowing easy access to synthetically as well as biologically important and structurally diverse ring-fused oxazines is developed. The method is operationally simple and highly di
- Mahato, Sujit,Haldar, Surajit,Jana, Chandan K.
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supporting information
p. 332 - 334
(2014/01/06)
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- Magnesium sulfate promoted efficient and green synthesis of aminoalkyl, amidoalkyl and diarylmethane derivatives
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Under solvent-free condition, magnesium sulfate promoted the synthesis of substituted aminoalkyl naphthols, amidoalkyl naphthols and diarylmethane derivatives in excellent yield. Robust dehydrating nature and mild Lewis acidity of magnesium sulfate was exploited to carry out all the transformations.
- Ganesan, S. Selva,Asaithampi
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p. 8380 - 8382
(2015/05/20)
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- Redox-neutral α,β-difunctionalization of cyclic amines
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In contrast to the continuously growing number of methods that allow for the efficient α-functionalization of amines, few strategies exist that enable the direct functionalization of amines in the β-position. A general redox-neutral strategy is outlined for amine β-functionalization and α,β-difunctionalization that utilizes enamines generated insitu. This concept is demonstrated in the context of preparing polycyclic N,O-acetals from simple 1-(aminomethyl)-β-naphthols and 2-(aminomethyl)-phenols. An unprecedented α,β-difunctionalization reaction of amines affords polycyclic N,O-acetals from simple 1-(aminomethyl)-β-naphthols or 2-(aminomethyl)-phenols. These transformations are redox-neutral and proceed in the absence of any additives.
- Chen, Weijie,Kang, Youngku,Wilde, Richard G.,Seidel, Daniel
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supporting information
p. 5179 - 5182
(2014/05/20)
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- Betti base as an efficient ligand for copper-catalyzed ullmann coupling of phenol with aryl halides
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GRAPHICAL ABSTRACT A simple, general, and highly efficient Betti base ligand has been developed for copper-catalyzed Ullmann coupling of phenol with aryl halides without the protection of an inert atmosphere. The reaction proceeds smoothly in the presence of K2CO3 as the base and dimethylsulfoxide as the solvent. The catalyst was reused several times with no evident loss of catalytic activity and is environmentally friendly.
- Yang, Li,Yang, Qichao,Shi, Jianxin,Wang, Yufang,Zhang, Mingjie
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supporting information
p. 2468 - 2477
(2014/08/05)
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- Copper-catalyzed regioselective intramolecular oxidative α-functionalization of tertiary amines: An efficient synthesis of dihydro-1,3-oxazines
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Traffic control: The hydroxy functional group directs the α-functionalization of tertiary amines, synthesizing 1,3-oxazines by C-O bond formation. Reaction occurs with both benzylic and non-benzylic amines. In the case of naphthoxazine synthesis, 100 % diastereoselectivity was observed. A tentative two-pathway mechanism is proposed for the reaction. Copyright
- Deb, Mohit L.,Dey, Suvendu S.,Bento, Isabel,Barros, M. Teresa,Maycock, Christopher D.
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supporting information
p. 9791 - 9795
(2013/09/23)
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- Application of 1-(α-aminobenzyl)-2-naphthols as air-stable ligands for pd-catalyzed Mizoroki-Heck coupling reaction
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Air-stable, easily accessible Mannich bases, 1-(α-aminobenzyl)-2- naphthols, are used as ligands in palladium-catalyzed Mizoroki-Heck reaction on a variety of substrates. High turnover numbers are observed for both the reactions with aryl bromides and iodides, while aryl chlorides are inert. Copyright Taylor & Francis Group, LLC.
- Chaudhary, Anju R.,Bedekar, Ashutosh V.
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experimental part
p. 1778 - 1785
(2012/04/10)
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- A competent pot and atom-efficient synthesis of Betti bases over nanocrystalline MgO involving a modified Mannich type reaction
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A simple, efficient, and eco-friendly method for the synthesis of 1-(α-aminoalkyl) naphthols, the Betti bases, has been carried out over a basic nanocrystalline MgO catalyst in aqueous condition. The method has been applied for the synthesis of a range of compounds with variable functionalities in excellent yield and selectivity.
- Karmakar, Bikash,Banerji, Julie
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experimental part
p. 4957 - 4960
(2011/10/08)
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- Convenient synthesis of 1-arylmethyl-2-naphthols
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A new environmentally benign, two-step procedure for the synthesis of 1-arylmethyl-2-naphthols in good to excellent yield is reported. It involves microwave-assisted facile formation of Mannich bases of 2-naphthol under solvent-free conditions and subsequ
- Paul, Nawal K.,Dietrich, Lindsay,Jha, Amitabh
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p. 877 - 888
(2007/10/03)
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- Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour
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A novel two-step procedure involving the formation of 1-arylidene-2- tetralones from 2-tetralone and subsequent Michael addition of a cyclic secondary amine on the alkenone followed by in situ aerial oxidation was developed to produce 2-naphthol Mannich bases. A simple microwave-assisted one-pot synthesis of 2-naphthol Mannich bases was also carried out under solvent-free conditions from 2-naphthol and corresponding aldehydes and amines in the presence of p-toluenesulfonic acid. The compounds of this series displayed interesting NMR behaviour. Extensive variable-temperature NMR investigations, including HSQC experiments, are herein reported. NMR results on the conformation in solution phase were found to be consistent with the X-ray crystal structure in the solid state.
- Jha, Amitabh,Paul, Nawal K.,Trikha, Smriti,Cameron, T. Stanley
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p. 843 - 853
(2007/10/03)
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- Substituted 1 and 2 naphthol mannich bases
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The invention relates to substituted 1 and 2 naphthol Mannich bases, a method for the production thereof, medicaments containing said compounds and the use of said compounds in the production of medicaments.
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- A modified Mannich-Type reaction catalyzed by VO(acac)2
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(Equation Presented) A fackile VO(acac)2-catalyzed in situ generation of iminium ions from amine N-oxides and their participation in a modified Mannich-type reaction is described.
- Hwang, Der-Ren,Uang, Biing-Jiun
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p. 463 - 466
(2007/10/03)
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- Solvent-free aminoalkylation of phenols and indoles assisted by microwave irradiation
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Phenols and indoles were aminoalkylated in a solvent-free and environmentally friendly Mannich reaction on acidic alumina assisted by microwave irradiation in good overall yields.
- Sharifi,Mirzaei,Naimi-Jamal
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p. 875 - 880
(2007/10/03)
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- Amino(hetero)arylmethylation of phenols with N-[α- Amino(hetero)arylmethyl]benzotriazoles
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N-[α-Amino(hetero)arylmethyl]benzotriazoles derived from a variety of (hetero)aromatic aldehydes were reacted with sodium phenolates to afford amino(hetero)arylmethylated phenols in high yields.
- Katritzky, Alan R.,Abdel-Fattah, Ashraf A. A.,Tymoshenko, Dmytro O.,Belyakov, Sergei A.,Ghiviriga, Ion,Steel, Peter J.
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p. 6071 - 6075
(2007/10/03)
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