- Synthesis, characterization and application of n,n-dimethyl-n-sulfoethan ammonium tetra-chloro aluminate: A novel micro-heterogeneous catalyst for synthesis of tri-arylmethanes
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A new solid catalyst was synthesized from an ionic liquid and heterogenised by changing the anion reaction. The new heterogeneous acidic catalyst was characterized by SEM images, EDS analysis, AFM images, Ft-IR, HNMR,13CNMR and Mass Spectroscop
- Azimi, Saeid,Mohamadighader, Niloofar
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p. 594 - 603
(2021/09/30)
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- Synthesis of symmetric triarylmethane derivatives catalyzed by AIL ionic liquid
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Abstract: An efficient, eco-friendly ionic liquid was described for the synthesis of symmetric triarylmethane derivatives via Baeyer condensation of N,N-dimethylaniline with different active aromatic aldehyde compounds using amide ionic liquid as a catalyst. The syntheses were achieved for the first time using amide ionic liquid as a catalyst eliminating the need for a volatile organic solvent. The advantages of this ionic liquid are low cost and operational simplicity.
- Kang, Li Q.,Gao, Han,Cai, Yue Q.
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- Catalyst free, three-component approach for unsymmetrical triarylmethanes (TRAMs)
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An efficient catalyst free, three-component, cascade approach has been designed and developed for the rapid assembly of unsymmetrical triarylmethane framework. The strategy employed aromatic aldehydes, Grignard reagents, and neutral aromatics as reaction
- Chinta, Bhavani Shankar,Baire, Beeraiah
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supporting information
p. 5381 - 5384
(2016/11/11)
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- Solvent-free synthesis of 4,4-diaminotriarylmethanes-leuco malachite materials in the presence of FePO4
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A fast, efficient and versatile route for the synthesis of 4,4-diaminotriarylmethanes is reported using N,N-dimethyl aniline and aryl aldehydes in presence of FePO4 under solvent-free condition at 100°C.
- Behbahani, Farahnaz K.,Khademloo, Elham
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p. 1507 - 1510
(2015/02/05)
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- Efficient synthesis of Bis(4-Dimethaminophenyl)arylmethanes and Bis(4-Diamethaminophenyl)alkanes using iodine reagent
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A novel synthetic utility of NaICl2 for the preparation of bis(4-dimethaminophenyl)arylmethanes and bis(4-dimethaminophenyl)alkanes is described. In the presence of an aqueous solution of NaICl2, the reaction of arenes with aromatic aldehydes gives corresponding triarylmethane derivatives regioselectively in moderate to good yields. The method is also useful for the preparation of diarylalkane derivatives by using aliphatic aldehydes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Bachhav, Harshal M.,Takale, Balaram S.,Telvekar, Vikas N.
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p. 1909 - 1914
(2013/05/21)
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- Halogen-free room-temperature bronsted acidic ionic liquid [Hmim]+ HSO4- as a recyclable green "dual reagent" catalysis for the synthesis of triarylmethanes (TRAM s) ;
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The halogen-free Brnsted acidic ionic liquid methylimidazolium hydrogen sulfate ([Hmim]+ HSO4-) acts as a very efficient catalyst for the one-pot, two-component Baeyer condensation of a variety of aromatic aldehydes with dimethyl or diethyl aniline at room temperature. This green reagent behaves as both catalyst and solvent; that is, it exhibits dual-reagent catalysis. The room-temperature acidic ionic liquid could be recycled several times with almost no loss in the yield of the reaction. This is the first report of the Baeyer synthesis with a halogen-free ionic liquid.
- Mukhopadhyay, Chhanda,Datta, Arup,Tapaswi, Pradip Kumar
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experimental part
p. 2453 - 2463
(2012/06/29)
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- Malachite Green Derivatives for Two-Photon RNA Detection
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The design, preparation and characterisation of a library of malachite green (MG) derivatives for two-photon RNA labelling is described. Some of these MG derivatives exhibit an increased affinity for an MG-aptamer, as well as improved two-photon sensitivi
- Lux, Jacques,Pena, Eduardo Jose,Bolze, Frederic,Heinlein, Manfred,Nicoud, Jean-Francois
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scheme or table
p. 1206 - 1213
(2012/07/03)
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- An efficient and convenient protocol for the synthesis of diaminotriarylmethanes
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A novel and efficient procedure was developed for the preparation of diaminotriarylmethanes through the Baeyer condensation of aromatic aldehydes and N,N-dimethylaniline or N,N-diethylaniline in the presence of niobium chloride under solvent-free conditio
- Hou, Jun-Tao,Gao, Jian-Wu,Zhang, Zhan-Hui
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experimental part
p. 495 - 499
(2011/12/16)
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- SbCl3-catalyzed one-pot synthesis of 4,4′-diamino- triarylmethanes under solvent-free conditions: Synthesis, characterization, and DFT studies
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A simple, efficient, and mild procedure for a solvent-free one-step synthesis of various 4,4′-diaminotriarylmethane derivatives in the presence of antimony trichloride as catalyst is described. Triarylmethane derivatives were prepared in good to excellent yields and characterized by elemental analysis, FTIR, 1H and 13C NMR spectroscopic techniques. The structural and vibrational analysis were investigated by performing theoretical calculations at the HF and DFT levels of theory by standard 6-31Gs *, 6-31G*/B3LYP, and B3LYP/cc-pVDZ methods and good agreement was obtained between experimental and theoretical results.
- Bardajee, Ghasem Rezanejade
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experimental part
p. 135 - 144
(2011/05/16)
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- ZrOCl2 catalyzed Baeyer condensation: A facile and efficient synthesis of triarylmethanes under solvent-free conditions
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A facile and efficient synthesis of an array of triarylmethanes by the Baeyer condensation of different arylaldehydes carrying activated and deactivated groups and N,N-dimethyIaniline using a catalytic amount of ZrOCI2 under solvent-free microwave irradiation conditions is described. Further, the catalytic activity of ZrOCI2 is compared with traditional Lewis acid catalysts and found that this synthetic method has the advantages of excellent yields (70-96%), shorter reaction time (few minutes) and solvent-free conditions.
- Reddy, Ch Sanjeeva,Nagaraj,Srinivas,Reddy
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experimental part
p. 248 - 254
(2009/12/03)
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- Baeyer condensation in chloroaluminate ionic liquid
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1-n-butylpyridinium chloroaluminate serves the dual purpose of a reaction medium and a Lewis acid catalyst for condensation of substituted benzaldehydes with N, N-dimethylaniline to obtain triarylmethanes (leuco bases) in good yields with significant reduction in reaction time and simplification of the workup process.
- Paul, Aniruddha M.,Khandekar, Amit C.,Khadilkar, Bhushan M.
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p. 168 - 169
(2007/10/03)
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- Montmorillonite clay catalysis VI: Synthesis of triarylmethanes via Baeyer condensation of aromatic aldehydes with N,N-dimethylaniline catalysed by montmorillonite K-10
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Triarylmethanes are synthesized in good to excellent yield via Baeyer condensation of aromatic aldehydes with N,N-dimethylaniline catalysed by montmorillonite K 10 at 100°C in the absence of solvent.
- Zhang, Zhan-Hui,Yang, Feng,Li, Tong-Shuang,Fu, Cheng-Guang
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p. 3823 - 3828
(2007/10/03)
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- Etudes sur les composes gem-diamines-V-Reactions d'anilines sur des composes gem-dimorpholines.
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A systematic study of gem-dimorpholino compounds, which produce aldehydes by hydrolysis, has shown that such compounds do indeed have aldehydic character and can be used in synthesis in place of the corresponding aldehydes.As part of this study we have examined the behaviour of such gem-dimorpholino compounds towards some nucleophilic reagents such as mercaptans, amides and anilines under acid conditions.We have found experimental conditions under which symmetrical geminal compounds are produced: dithioacetals, gem-bis(acylamino), gem-diamino and gem-diaryl compounds.We have thus developed several new synthetic methods which compare favourably with existing methods.In most cases we have been able to show that the reaction proceeds by an intermediate in which only one of the morpholino groups has been replaced by the nucleophile.In this paper we report on the condensation of some anilines with gem-dimorpholino compounds.N,N-dimethylaniline condenses with gem-dimorpholino compounds as with the corresponding aldehydes to give gem-diaryl compounds.The case of primary arylamines is remarkable for the different results obtained.As could be expected from our most recent results, most of the condensation products are complex mixtures which are either non-distillable and non-crystallisable oils or glassy solids with indistinct melting points.It is often impossible to isolate any pure chemical substance from these mixtures.We shall thus only describe certain cases: the behaviour of 2,6-xylidine is particularly interesting.Under certain conditions this aniline derivative can condense on the aromatic ring similarly to N,N-dimethylaniline.The initial product of the reaction is an aldimine or "anil".Benzaldimines which are stabilised by conjugation do not react further while phenylglyoxaldimines are transformed into gem-diaryl compounds by heating in acetic acid. 2,5-dimethoxyaniline also condenses by way of the aromatic ring to give a gem-diaryl compound but the corresponding aldimine could not be shown to be an intermediate. 2-nitro and 3-nitroaniline, in which the aromatic ring is deactivated, can only condense by the nitrogen atom to give gem-diamino compounds.In summary, we think that primary arylamines in acetic acid condense with gem-dimorpholino compounds preferentially on the nitrogen atom of the amino group.These compounds can subsequently, according to their stability, rearrange provided that the aromatic ring is activated by electron-donating substituents.It still remains to be determined if there is a definite point at which a primary aniline starts to act as an ambifunctional nucleophile.
- Floc'H, Yves Le,Morvan, Jean-Marcel,Brault, Auguste
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p. 157 - 162
(2007/10/02)
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