- Bromodimethylsulfonium bromide mediated Michael addition of amines to electron deficient alkenes
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Bromodimethylsulfonium bromide has been found to be an efficient catalyst for the Michael addition of a wide variety of amines to electron deficient alkenes at room temperature. The protocol is very simple and chemoselective. Aliphatic and benzylic amines undergo conjugate addition within a very short period under solvent-free conditions and provide excellent yields of products.
- Khan, Abu T.,Parvin, Tasneem,Gazi, Sarifuddin,Choudhury, Lokman H.
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- Microwave-assisted, rapid, solvent-free aza-michael reaction by perchloric acid impregnated on silica gel
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Highly efficient solvent-free aza-Michael additions of a variety of amines to,-unsaturated carbonyl compounds under microwave-irradiation conditions catalyzed by perchloric acid impregnated on silica gel (HClO4/SiO2) is reported. The reactions are completed within 2-7min in a microwave oven to produce the corresponding adducts in excellent yields, and the catalyst can be recovered and reused.
- Singh, Surya Prakash,Kumar, T. Vijaya,Chandrasekharam,Giribabu,Reddy, P. Yella
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Read Online
- SEGREGATED FLUORINATED ESTERS
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Segregated fluorinated esters are described that are useful as dielectric fluids in electrical devices and as heat transfer agents.
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Page/Page column 29
(2016/05/24)
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- Lipase-catalyzed aza-michael reaction on acrylate derivatives
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A methodology has been developed for an efficient and selective lipase-catalyzed aza-Michael reaction of various amines (primary and secondary) with a series of acrylates and alkylacrylates. Reaction parameters were tuned, and under the optimal conditions it was found that Pseudomonas stutzeri lipase and Chromobacterium viscosum lipase showed the highest selectivity for the aza-Michael addition to substituted alkyl acrylates. For the first time also, some CLEAs were examined that showed a comparable or higher selectivity and yield than the free enzymes and other formulations.
- Steunenberg, Peter,Sijm, Maarten,Zuilhof, Han,Sanders, Johan P. M.,Scott, Elinor L.,Franssen, Maurice C. R.
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p. 3802 - 3813
(2013/06/05)
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- Guanidine-based task-specific ionic liquids as catalysts for aza-Michael addition under solvent-free conditions
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An efficient and facile protocol for aza-Michael addition of aliphatic and aromatic amines to electron-deficit alkenes using [TMG][Lac] as catalyst under solvent-free conditions was established.
- Ying, Anguo,Zheng, Ming,Xu, Haidan,Qiu, Fangli,Ge, Changhua
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experimental part
p. 883 - 890
(2012/04/17)
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- Aza-Michael addition of aliphatic or aromatic amines to α,β-unsaturated compounds catalyzed by a DBU-derived ionic liquid under solvent-free conditions
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A task-specific ionic liquid, 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate has been successfully used as a catalyst for aza-conjugate addition of aliphatic or aromatic amines to various electron deficient alkenes under solvent-free conditions and at room temperature. The catalyst can be reused for six times without noticeable loss of activity.
- Ying, An-Guo,Liu, Luo,Wu, Guo-Feng,Chen, Gang,Chen, Xin-Zhi,Ye, Wei-Dong
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experimental part
p. 1653 - 1657
(2009/06/28)
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- Imidazolium-based polymer supported gadolinium triflate as a heterogeneous recyclable Lewis acid catalyst for Michael additions
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A heterogeneous Lewis acid catalytic system has been developed by incorporating gadolinium triflate on to poly[styrene-co-(1-((4-vinylphenyl)methyl)-3-methylimidazolium) tetrafluoroborate] (1-Gd(OTf)3), and the catalytic activity of this system has been examined for Michael additions of amines and thiols to α,β-unsaturated esters and acrylonitrile. The reactions proceed in moderate to excellent yields in the presence of catalytic system 1-Gd(OTf)3. The catalytic system could be efficiently recycled and reused.
- Alleti, Ramesh,Oh, Woon Su,Perambuduru, Meher,Ramana,Prakash Reddy
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p. 3466 - 3470
(2008/09/21)
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- Significant rate acceleration of the aza-Michael reaction in water
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The addition of amines to conjugated alkenes has been carried out in water at room temperature very efficiently without any catalyst. Significant rate acceleration of this reaction is observed in water compared to organic solvents.
- Ranu, Brindaban C.,Banerjee, Subhash
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p. 141 - 143
(2007/10/03)
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- ZrOCl2·8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions
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At room temperature, ZrOCl2·8H2O on montmorillonite K10 efficiently catalyzes conjugate addition of amines to a variety of conjugated alkenes such as α,β-unsaturated carbonyl compounds, carboxylic esters, nitriles and amides under solvent-free conditions. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency.
- Hashemi, Mohammed M.,Eftekhari-Sis, Bagher,Abdollahifar, Amir,Khalili, Behzad
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p. 672 - 677
(2007/10/03)
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- Polyvinyl pyridine as a novel solid heterogeneous, recyclable catalyst for aza-Michael reaction
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Polyvinyl pyridine (PVP) is prepared by radical polymerization of 4-vinyl pyridine. PVP was used as a heterogeneous basic catalyst for the aza-Michael reaction of secondary amines and carbamates with α,β-unsaturated esters, cyanides and ketones to obtain the corresponding adducts in excellent yields (70-90%). Georg Thieme Verlag Stuttgart.
- Raje, Vivek P.,Bhat, Ramakrishna P.,Samant, Shriniwas D.
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p. 2676 - 2678
(2008/09/16)
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- RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles
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The 1,4-conjugate addition of primary, secondary and aromatic amines, thiols, and carbamate to α,β-unsaturated compounds mediated by a catalytic amount (0.5 mol%) of RuCl3 in poly(ethylene glycol) (PEG) provides the desired β-substituted carbonyls in high yields. In particular, we found that primary aliphatic and aromatic amines produced the single adducts as the sole products in very high yields with RuCl3-PEG. RuCl 3-PEG was readily recycled via solvent precipitation with efficient recyclability as evidenced by high yields. Its properties of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, and efficient recyclability make RuCl3-PEG suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls. Georg Thieme Verlag Stuttgart.
- Zhang, Huaxing,Zhang, Yuhong,Liu, Leifang,Xu, Hailiang,Wang, Yanguang
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p. 2129 - 2136
(2007/10/03)
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- Boric acid: A novel and safe catalyst for aza-Michael reactions in water
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Boric acid efficiently catalyzes the conjugate addition of aliphatic amines to α,β-unsaturated compounds to produce β-amino compounds, with great alacrity and excellent yields, in water under mild conditions. Aromatic amines do not participate effectively in the reaction.
- Chaudhuri, Mihir K.,Hussain, Sahid,Kantam, M. Lakshmi,Neelima
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p. 8329 - 8331
(2007/10/03)
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- Anthraquinone-photocatalysed addition of amines toα,β-unsaturated esters: a novel route to indolizidone, pyrrolizidone and related ring systems
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The indolizidone 9, the pyrrolizidone 14, a mixture of heliotridone 15a and pseudoheliotridone 15b and the lactam 19 have been synthesized in a one-step anthraquinone-photocatalysed reaction of the corresponding amines, piperidine 1, pyrrolidine 10 and morpholine 16, with α,β-unsaturated esters.
- Das, Suresh,Kumar, J. S. Dileep,Shivaramayya, K.,George, M. V.
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p. 1797 - 1800
(2007/10/02)
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