cas 33611-43-7, METHYL 3-MORPHOLINOPROPIONATE

Articles about 33611-43-7Total 63 be found

Article title
Article abstract
Author
Journal number and time
Download

Ni(II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins
Ni(II) complexes containing chiral tridentate ferrocenyl phosphines (Ni(PPP)) have been found to efficiently catalyse the hydroamination of activated olefins with both anilines and aliphatic amines at r.t. (TON up to 71, TOF up to ca. 3 h-1, and enantioselectivities up to 69% ee).
Fadini, Luca,Togni, Antonio
p. 30 - 31
(2003)
Read Online

Bio-heterogeneous Cu(0)NC@PHA for n-aryl/alkylation at room temperature
A pure cellulose was derived from waste fibre and it was chemically modified to a hydroxamic acid ligand. The poly(hydroxamic acid) was treated with an aqueous copper solution to afford the greenish stable five-membered copper complex; namely Cu(II)@PHA. Further, the Cu(II)@PHA was treated with a reducing agent hydrazine hydride to give brown colour cellulose supported copper nanocomplex (Cu(0)NC@PHA). The Cu(0)NC@PHA was characterised by ATR-FTIR, FE-SEM & EDS, TEM, ICP-OES, TGA, XRD and XPS analyses. The cellulose-based Cu(0)NC@PHA was used for the n-aryl/alkylation (Michael addition) reaction with a variety of α,β-unsaturated Michael acceptors to produce the corresponding n-aryl/alkyl products with an excellent yield at room temperature. The Cu(0)NC@PHA showed extraordinary stability and it was easily filtered out from the reaction mixture and may potentially recycled up to five times without loss of its original catalytic ability.
Jian Fui, Choong,Lutfor Rahman, Md,Musta, Baba,Sani Sarjadi, Mohd,Sarkar, Shaheen M.,Xin Ting, Tang
(2021/06/28)

A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions
The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.
Zelenay, Benjamin,Munton, Peter,Tian, Xiaojie,Díez-González, Silvia
p. 4725 - 4730
(2019/08/01)

Green synthesis of Ag@Au bimetallic regenerated cellulose nanofibers for catalytic applications
The green synthesis of nanocomposites has attracted huge consideration in recent years due to its positive environmentally friendly impact. The present study reports the first bimetallic Ag-Au cellulose nanofiber composite (Ag@Au/CNCs) prepared via a very simple green preparation method. An aqueous leaves extract of Moringa oleifera was used to obtain the bimetallic Ag@Au/CNC nanocomposite. High-resolution transmission electron microscopy (HRTEM) observations revealed the successful formation of triangle, hexagonal, and spherical shapes of well-combined Ag-Au nanoparticles on the regenerated cellulose nanofiber surface. Further, the formation of Au-Ag bimetallic nanostructures was confirmed by X-ray photoelectron spectroscopy (XPS) and X-ray crystallography (XRD) results. The resultant bimetallic Ag@Au/CNC catalyst was found to perform remarkably well in the reduction of nitrophenols. The bimetallic Ag@Au/CNC catalyst gave excellent kapp values of 15.59 and 22.83 × 10-3 s-1 for the 2- A nd 4-nitrophenol reduction process, respectively. To our delight, the Ag@Au/CNC catalyst was found to perform well in the aza-Michael reaction. The catalytic activity of Ag@Au/CNCs was compared with mono-metallic Ag/CNCs, Au/CNCs, and other reported catalysts. Based on the results obtained, the high synergy of Ag@Au/CNCs was explained. A possible mechanism is proposed for the Ag@Au/CNC-catalyzed nitrophenol reduction and aza-Michael reactions.
Gopiraman, Mayakrishnan,Saravanamoorthy, Somasundaram,Baskar, Ramaganthan,Ilangovan, Andivelu,Ill-Min, Chung
p. 17090 - 17103
(2019/11/14)

Cultivation of a Cu/HMPC catalyst from a hyperaccumulating mustard plant for highly efficient and selective coupling reactions under mild conditions
Cu-containing activated carbon (eco-catalyst, Cu/HMPC, where 'C' defines 'carbon') was derived from a metal-hyperaccumulating mustard plant (HMP) by a simple chemical activation method. Transmission electron microscopy/selected area diffraction (HRTEM/SAED) results revealed that the Cu/HMPC has mainly three types of morphology [sheet-like morphology (2D), hollow-spheres (3D) and needle-like structures (1D)] which are interconnected. HRTEM-SAED, Raman and X-ray photoelectron spectroscopy (XPS) results confirmed the existence of Cu oxide species in Cu/HMPC. Content of Cu in Cu/HMPC was determined to be 1.03 wt%. The quality of graphitization in Cu/HMPC was discussed by using Raman and XRD results. The BET surface area of Cu/HMPC was determined to be 620.8 m2 g-1. The Cu/HMPC actively transformed a wide range of amines to imines under very mild reaction conditions. The catalyst Cu/HMPC gave products in excellent yields (98-61%) with very high TON/TOF values (1512/339-833/35 h-1). To the best of our knowledge, this is the most efficient Cu-based heterogeneous eco-catalyst for the synthesis of imines among those reported to date. The Cu can be recovered from used Cu/HMPC by a simple HCl treatment. Versatility, heterogeneity and reusability of Cu/HMPC were tested. A possible mechanism has been proposed.
Gopiraman, Mayakrishnan,Wei, Kai,Zhang, Ke-Qin,Chung, Ill-Min,Kim, Ick Soo
p. 4531 - 4547
(2018/02/09)

Tapioca cellulose based copper nanoparticles for chemoselective N-alkylation
Biomaterials as a support for catalysts are of prime importance. Tapioca root which is an abundant biopolymer source was used to synthesize cellulose supported bio-heterogeneous poly(hydroxamic acid) copper nanoparticles (CuN@PHA) and was characterized by Fourier transform infrared spectroscopy (FTIR), ultraviolet-visible spectroscopy (UV-Vis), field emission scanning electron microscopy (FESEM), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma atomic emission spectroscopy (ICP-AES), transmission electron microscopy (TEM) analyses. The tapioca cellulose supported CuN@PHA (50 mol ppm) effectively catalyzed N-alkylation reaction of aliphatic amines with α,β-unsaturated compounds to give the corresponding alkylated products. High yields up to 95% were achieved for the converted products. The reusability of the cellulose supported nanoparticles was found to be excellent with no significant reduction of its catalytic activity over several cycles. The catalyst showed high catalytic activity having turnover number (TON) 18000 and turnover frequency (TOF) 2250 h-1.
Islam, Md. Shaharul,Mandal, Bablu Hira,Biswas, Tapan Kumar,Rahman, Md. Lutfor,Rashid,Tan, Suat-Hian,Sarkar, Shaheen M.
p. 550 - 557
(2017/01/05)

MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE
PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
-
Paragraph 0051; 0053; 0054

(2018/07/03)

Nickel(II) N-Heterocyclic Carbene Complexes: Versatile Catalysts for C–C, C–S and C–N Coupling Reactions
A variety of NiII complexes with a wide range of electronic and steric properties, bearing picolylimidazolidene ligands (a–g) and Cp (Cp = η5-C5H5; 2a–f) or Cp* (Cp* = η5-C5Me5; 3a, c, g) groups, have been synthesised and characterised by using NMR spectroscopy and single-crystal X-ray crystallography. The complexes have been used as precatalysts for a wide range of catalytic transformations, which most likely involve a Ni0/NiII catalytic cycle. In particular, the new well-defined 2a, 2c, 3a and 3c complexes have demonstrated great efficiency and versatility towards Suzuki–Miyaura coupling reactions, hydroamination of activated olefins and C–S cross-coupling reactions of aryl halides and thiols under mild conditions.
Junquera, Lourdes Benítez,Fernández, Francys E.,Puerta, M. Carmen,Valerga, Pedro
supporting information
p. 2547 - 2556
(2017/05/29)

Waste corn-cob cellulose supported bio-heterogeneous copper nanoparticles for aza-Michael reactions
Bio-heterogeneous poly(amidoxime) copper nanoparticles were prepared on the modified surface of waste corn-cob cellulose through a graft copolymerization process. The Cu-nanoparticles (0.05 mol% to 50 mol ppm) selectively promoted the aza-Michael reaction of aliphatic amines to give the corresponding alkylated products at room temperature in methanol. The supported nanoparticles were easy to recover and reused eight times without a significant loss of their activity.
Sarkar, Shaheen M.,Sultana,Biswas, Tapan Kumar,Rahman, Md. Lutfor,Yusoff, Mashitah Mohd
p. 497 - 502
(2016/01/12)

Ionic liquid catalytic amine with the α, β-unsaturated electron deficient receptor method
The invention relates to a method for catalyzing amines and alpha, beta-unsaturated electron-deficient acceptors by an ionic liquid. The method comprises the following steps: by taking the ionic liquid as a catalyst, carrying out a catalytic addition reaction on alpha, beta-unsaturated electron-deficient acceptors such as amines, acrylate and acrylonitrile at room temperature and at normal pressure, and carrying out column chromatography to obtain a corresponding addition product; magnetically stirring at room temperature without a solvent, after reaction, extracting the ionic liquid by water and ethyl acetate; carrying out column chromatography on an organic phase to obtain a product; and re-putting the filtrate with the water phase of the ionic liquid without vapor at high temperature in vacuum to react. Through verification, the product can be used as a catalytic reaction system which is repeatedly used for 6 times, and no remarkable reaction yield reduction is discovered. The method is simple to operate, high in yield, good in reusability of the catalytic reaction system and mild reaction condition and has a good industrialized prospect.
-
Paragraph 0044-0045

(2017/02/09)

Poly(hydroxamic acid) functionalized copper catalyzed C-N bond formation reactions
Highly active poly(hydroxamic acid) functionalized copper catalysts were synthesized by the surface modification of khaya cellulose through graft copolymerization and subsequent hydroximation processes. The prepared catalysts were well characterized by FTIR, FESEM, HRTEM, ICP-AES, UV-vis and XPS analyses. The supported catalysts effectively promoted C-N bond formation reactions and provided excellent yields of the corresponding products under mild reaction conditions. The catalysts were easy to recover from the reaction mixture and were reused several times without any significant loss of their catalytic activity.
Islam, Md. Shaharul,Mandal, Bablu Hira,Biswas, Tapan Kumar,Rahman, Md. Lutfor,Rashid,Tan, Suat-Hian,Sarkar, Shaheen M.
p. 56450 - 56457
(2016/07/06)

Lipase immobilization on hyroxypropyl methyl cellulose support and its applications for chemo-selective synthesis of β-amino ester compounds
The present study carried out the synthesis of β-amino ester compounds using lipase immobilized on hyroxypropyl methyl cellulose (HMC) support. Initially various lipases (biocatalysts) from different origin were immobilized and subsequently screened to obtain the robust biocatalyst. The lipase Pseudomonas fluorescence (PFL) immobilized on HMC was displayed highest lipase activity, protein content and retention of activity. The physical and biochemical characterization verified immobilization of lipase PFL on the HMC support. This immobilized biocatalyst HMC:PFL (3.5:1) was successfully applied for the practical biocatalytic applications to synthesize variety of β-amino esters. Various eight reaction parameters were optimized in details to achieve the maximum yield and chemo-selectively. The developed biocatalytic protocol was successfully applied to synthesize different industrially important β-amino esters compounds (21 substrates) with an excellent yield (>90%) and remarkable chemo selectivity (>94%). Interestingly, the immobilized HMC:PFL lipase showed 2.1–2.5 folds higher bio-catalytic activity and five times recyclability as compared to the free PFL. The plausible mechanism for lipase catalyzed synthesis of β-amino ester compounds was also proposed.
Badgujar, Kirtikumar C.,Bhanage, Bhalchandra M.
p. 1420 - 1433
(2016/10/03)

Synthesis and catalytic activity of porous polymer containing ionic liquid structures
A novel porous polymer containing ionic liquid (IL) structures was synthesized via quternization and condensation of 4-vinylpyridine and p-xylylene dichloride. The ionic liquid structures were incorporated in the polymeric framework and for this reason bulky IL molecules can hardly block pores and neutralize active sites. The polymer shows a high BET surface area and easily accessible active sites. Catalytically the polymer is very active in Michael additions with averaged yields over 96.0% achieved after short reaction times. The high BET surface, remarkable activity, operational simplicity, wide applicability and improved stability are the key properties of the polymer.
Li, Junqiao,Lu, Wei,Li, Weifeng,Liang, Xuezheng
p. 840 - 846
(2016/12/07)

[CH3COO]: Efficient and recyclable catalyst for aza-Michael addition of α, β-unsaturated compounds and amines under solvent-free conditions
The recyclable ionic liquid [ADPQ][CH3COO] has been used as catalyst for aza-Michael addition of amines to α, β-unsaturated compounds to produce β-amino compounds. The reactions were complete in a few hours with high yields. The ionic liquid can be recycled and reused six times without noticeable decrease of catalytic activity.
Gao, Xiaochong,Gao, Ruichang
p. 9101 - 9112
(2015/03/04)

Efficient and reusable ionic liquid stabilized magnetic cobalt nanoparticles as catalysts for aza- and thia-Michael reactions
-
Dewan, Manika,De, Arnab,Mozumdar, Subho
p. 92 - 96
(2015/02/05)

Synthesis of a crosslinked polymer with a benzyl(triphenyl)phosphonium ionic liquid moiety and its catalytic activity
A novel crosslinked polymer with a benzyl(triphenyl)phosphonium ionic liquid moiety was synthesized from triphenylphosphine and p-xylylene dichloride. The bulky IL molecules were inlaid in the polymeric framework, which avoided pore blocking and IL moiety release. The polymer had a high BET surface area and accessible active sites. The polymer was applied to catalyze the aza-Michael additions and gave average yields over 95.0% in several minutes. The polymer had several advantages such as high BET surface area, high activity and high stability, which hold great potential for green chemical processes.
Liang, Xuezheng
p. 99448 - 99453
(2015/12/04)

Carbon dioxide as a reversible amine-protecting agent in selective Michael additions and acylations
Carbon dioxide can be used as a temporary protecting group for amines. A carbamic acid is formed reversibly when CO2 is bubbled through a solution of a sufficiently basic primary amine at room temperature and atmospheric pressure. This reaction is employed for the protection of the amine functionality in several reactions at room temperature where inter- or intramolecular selectivity is desired. The concept is demonstrated for the selective Michael additions to methyl acrylate of a normally less reactive sulfonamide in the presence of a strong amine nucleophile, or of a cyclic secondary amine in the presence of an aliphatic primary amine, or of a β-ketoester in the presence of amines. The selective acylation of an alcohol in the presence of an amine can be achieved under a CO2 atmosphere as well.
Peeters, Annelies,Ameloot, Rob,De Vos, Dirk E.
p. 1550 - 1557
(2013/09/24)

Designing anti-inflammatory drugs from parasitic worms: A synthetic small molecule analogue of the acanthocheilonema viteae product ES-62 prevents development of collagen-induced arthritis
In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects on relevant macrophage cytokine responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in an in vivo model of inflammation, collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development.
Al-Riyami, Lamyaa,Pineda, Miguel A.,Rzepecka, Justyna,Huggan, Judith K.,Khalaf, Abedawn I.,Suckling, Colin J.,Scott, Fraser J.,Rodgers, David T.,Harnett, Margaret M.,Harnett, William
supporting information
p. 9982 - 10002
(2014/01/17)

Lipase-catalyzed aza-michael reaction on acrylate derivatives
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.
p. 3802 - 3813
(2013/06/05)

Chemo/regioselective Aza-Michael additions of amines to conjugate alkenes catalyzed by polystyrene-supported AlCl3
A simple and efficient procedure is presented for Aza-Michael additions of various amines with conjugate alkenes bearing electron withdrawing group catalyzed by polystyrene-supported aluminum chloride (Ps-AlCl3) without the use of any solvents. The catalyst shows high catalytic activity for both aromatic amines and aliphatic amines. Chemoselective additions of the two types of amines with conjugate alkenes are achieved. Regioselective additions of two different amino groups in one molecule proceed smoothly. Ps-AlCl 3 has better recyclability and can be reused several times without apparent loss of activity.
Dai, Liyan,Zhang, Yi,Dou, Qianqian,Wang, Xiaozhong,Chen, Yingqi
p. 1712 - 1716
(2013/03/13)

Selective and nonselective aza-michael additions catalyzed by a chiral zirconium bis-diketiminate complex
Reaction of the chiral bis-diketiminate complex rac- or (R,R)-C 6H10(nacnacXyl)2ZrCl2 with AgOTf yielded the corresponding bis-triflate complex. The complex geometry changes from distorted octahedral in the dichloride complex to a pseudotetrahedral coordination involving π coordination of the diketiminate ligands. The bis-triflate complex is highly active for aza-Michael additions with turnover frequencies of 20000/h for the addition of morpholine to acrylonitrile and 1000/h for the addition of morpholine to methacrylonitrile. The enantioselectivities of the latter reaction in various solvents were low, never surpassing 19% ee. The reaction is first-order in olefin concentration and second order in amine concentration, which is explained by its participation as a base in the reaction mechanism. The presence of catalytic amounts of triethylamine slightly increases the observed rate constants and reduces the reaction order in amine to first order. Other activated alkenes such as methacrylonitrile, crotonitrile, methyl acrylate, and cyclohexenone can be employed, but no reactivity is observed toward styrene or vinyl ethers. Primary amines, secondary amines, and anilines can be employed as nucleophiles with activities correlating with their nucleophilicity, but the catalyst is unstable in the presence of alcohols.
El-Zoghbi, Ibrahim,Kebdani, Myriam,Whitehorne, Todd J. J.,Schaper, Frank
p. 6986 - 6995
(2014/01/06)

Ultrasound-assisted aza-Michael reaction in water: A green procedure
The conjugate addition of amines to conjugated alkenes (commonly known as aza-Michael reaction) constitutes a key step for the synthesis of various complex natural products, antibiotics, α-amino alcohols and chiral auxiliaries. Ultrasound-induced addition of several amines to α, β-unsaturated ketones, esters and nitriles has been carried out very efficiently in water as well as under solvent-free conditions. No catalysts or solid supports have been used in this method. Remarkable enhancement of reaction rate has been observed in water under ultrasound-induced method. This environmentally benign procedure has provided clean formation of the products with better selectivity.
Bandyopadhyay, Debasish,Mukherjee, Sanghamitra,Turrubiartes, Luis C.,Banik, Bimal K.
experimental part
p. 969 - 973
(2012/05/20)

Ecofriendly and efficient procedure for hetero-Michael addition reactions with an acidic ionic liquid as catalyst and reaction medium
1-Methylimidazolium trifluoroacetate ([Hmim]-TFA) is reported as a cost-effective catalyst for a simple and environmentally benign hetero-Michael reaction. [Hmim]TFA works both as reaction medium and catalyst. The reaction is applicable to various aromatic sulfur and nitrogen nucleophiles. This method has advantages such as high yields, short reaction time, and simple workup. The catalyst could be recycled several times without any loss of activity.
Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh,Baghbanzadeh, Mostafa
experimental part
p. 109 - 112
(2012/06/30)

Guanidine-based task-specific ionic liquids as catalysts for aza-Michael addition under solvent-free conditions
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
experimental part
p. 883 - 890
(2012/04/17)

Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media
A green approach to the Aza-Michael addition reaction between an amine and α,β-unsaturated compounds has been achieved by conventional as well as non-conventional methods. The reaction is catalyzed by cesium fluoride (CsF) in aqueous media at ambient temperature to afford the product in excellent yield. Ultrasound irradiation has been used as a non-conventional energy source, which reduces the reaction time with improved product yield.
Labade, Vilas B.,Pawar, Shivaji S.,Shingare, Murlidhar S.
experimental part
p. 1055 - 1059
(2012/07/27)

Aza-Michael reactions in water using functionalized ionic liquids as the recyclable catalysts
Some recyclable SO3H-functionalized ionic liquids have been used as catalysts in water for the aza-Michael reactions of amines with α,β-unsaturated compounds to produce β-amino compounds. High yields of the products, short reaction times, mild reaction conditions, simple experimental procedure, reusable catalysts and no obvious loss of the catalytic activity make this protocol a contribution to organic chemistry.
Liu,Lu,Gu,Lu
experimental part
p. 775 - 781
(2012/06/18)

Complex containing a Lewis acid and Bronsted acid for the catalytic reactions of aza-Michael addition
The novel efficient complex catalyst containing a Lewis acid and a Bronsted acid have been prepared by the reaction of proline ion liquid and cuprous iodide. The catalyst was characterized by FT-IR techniques using pyridine as probe molecule. A fast, mild, and quantitative procedure for aza-Michael addition reactions between various amines and α,β- unsaturated carbonyl compounds and nitriles has been developed using the novel complex catalyst. The results showed that the novel catalyst owned high activities for the reactions with excellent yields within 1 min.
Mao, Xin-Xin,Wang, Jiao,Xia, Qun-Hua,Shen, Yong-Miao
experimental part
p. 525 - 528
(2011/10/31)

Synthesis of a novel ionic liquid with both Lewis and Br?nsted acid sites and its catalytic activities
The novel ionic liquid with both Lewis and Br?nsted acid sites has been synthesized and its catalytic activities for acetalization and Michael addition were investigated carefully. The novel ionic liquid was stable to water and could be used in aqueous solution. Furthermore, the molar ratio of the Lewis and Br?nsted acid sites could be adjusted according to different reactions. The results showed that the novel ionic liquid was very efficient for the traditional acid-catalyzed reactions with good to excellent yields in short time.
Liang, Xuezheng,Qi, Chenze
experimental part
p. 808 - 812
(2012/01/04)

POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS
A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising recurring units containing a non-leaving hydroxyl group represented by formula (1) wherein R1 is H, methyl or trifluoromethyl, X is a single bond or methylene, m is 1 or 2, and the hydroxyl group attaches to a secondary carbon atom. The composition is improved in resolution when processed by lithography.
-
(2010/04/23)

Catalyzed synthesis of β-amino acids esters
-
Dokichev,Latypova,Shakirov,Biglova,Talipov
experimental part
p. 755 - 757
(2010/10/02)

Novel efficient procedure for the conjugate addition of amines to electron deficient alkenes
The novel efficient procedure has been developed for the conjugate addition of amines to electron deficient alkenes using the novel SO3H functionalized ionic liquid as catalyst. The results showed that the novel catalyst owned high activities for the reactions with excellent yields within several minutes. Various amines and electron deficient alkenes were successfully transformed to the corresponding products in the catalytic system. Operational simplicity, without need of any solvent, low cost of the catalyst used, room temperature, high yields, reusability, excellent chemoselectivity and wide applicability are the key features of this methodology.
Sun, Xudong,Du, Yijun,Li, Chunqing,Qi, Chenze
experimental part
p. 653 - 656
(2011/02/16)

Microwave-induced aza-michael reaction in water: A remarkably simple procedure
Microwave-induced fast addition of several amines to conjugated carbonyl compounds has been carried out in water very efficiently in the absence of any catalyst. Copyright
Kall, Andrea,Bandyopadhyay, Debasish,Banik, Bimal K.
experimental part
p. 1730 - 1735
(2010/07/14)

A comparison between nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in hydroamination of activated olefins
A comparison is drawn between the nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in the hydroamination of activated olefins. Though all of the newly designed nickel and palladium precatalysts, trans-[1-i-propyl-4-R-1,2,4-triazol-5-ylidene]2MBr2 [R = Et, M = Ni (1b); R = Et, M = Pd (1c); R = CH2CHCH2, M = Ni (2b) and R = CH2CHCH2, M = Pd (2c)], are moderately active for hydroamination reaction of a variety of secondary amines viz. morpholine, piperidine, pyrrolidine and diethylamine with activated olefins like, acrylonitrile, methyl acrylate, ethyl acrylate and t-butyl acrylate at room temperature in 1 hour, the nickel complexes (1b and 2b) exhibited superior activity compared to its palladium counterparts (1c and 2c). The better performance of the nickel complexes has been correlated to the more electron deficient metal center in the nickel 1b and 2b complexes than in the palladium 1c and 2c analogs based on the density functional theory studies. The 1b-c and 2b-c complexes were synthesized by the reaction of 1-i-propyl-4-R-1,2,4- triazolium bromide [R = Et (1a) and R = CH2CHCH2 (2a)] with MCl2 [M = Ni, Pd] in presence of NEt3 as a base. The Royal Society of Chemistry 2010.
Dash, Chandrakanta,Shaikh, Mobin M.,Butcher, Ray J.,Ghosh, Prasenjit
experimental part
p. 2515 - 2524
(2010/05/14)

Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates
An efficient protocol for the regioselective aza-Michael addition of amines with acrylates using CaL B as a biocatalyst at 60 °C has been developed. The reaction is applicable to a wide variety of primary and secondary amines with different acrylates to synthesize the corresponding β-amino esters with good yields. An alternative route for the synthesis of higher β-amino esters through the additional transesterification step is also studied and was found effective.
Dhake, Kishor P.,Tambade, Pawan J.,Singhal, Rekha S.,Bhanage, Bhalchandra M.
experimental part
p. 4455 - 4458
(2010/09/20)

Leishmanicidal potential of N-substituted morpholine derivatives: Synthesis and structure-activity relationships
A series of N-substituted morpholines 2-20 was synthesised by reacting various acid chlorides and alkyl halides with morpholine (1). All of the synthesised compounds 2-20 were screened for their leishmanicidal effects using amphotericin B (IC50 = 0.24 μg L-1) and pentamidine (IC50 = 2.56 μg mL-1) as standards and a structure-activity relationship (SAR) study was established. The compounds 2 (IC50 = 48 μg mL-1), 3 (IC50 = 30.0 μg mL-1), 10 (IC50 = 41.0 μg mL-1), 15 (IC50 = 33.0 μg mL-1), 16 (IC50 = 35.0 μg mL-1) and 20 (IC50 = 47.0 μg mL-1) showed weak leishmanicidal activities.
Khan, Khalid Mohammed,Khan, Muhammad Zarrar,Taha, Muhammad,Maharvi, Ghulam Murtaza,Saify, Zafar Saeed,Parveen, Shahnaz,Choudhary, Muhammad Iqbal
experimental part
p. 479 - 484
(2010/06/21)

Highly efficient Michael addition reaction of amines catalyzed by silica-supported aluminum chloride
Aliphatic and aromatic amines undergo smooth nucleophilic addition to α,β-unsaturated compounds in the presence of a catalytic amount of silica-supported aluminum chloride at 60°C and under solvent-free conditions to produce the corresponding β-amino compounds in excellent yields. This method is simple and convenient and works efficiently under mild conditions. This catalyst can used again without losing its activity three times. Copyright Taylor & Francis Group, LLC.
Saidi, Mohammad R.,Pourshojaei, Yaghoub,Aryanasab, Fezzeh
experimental part
p. 1109 - 1119
(2009/09/08)

Aza-Michael addition of aliphatic or aromatic amines to α,β-unsaturated compounds catalyzed by a DBU-derived ionic liquid under solvent-free conditions
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
experimental part
p. 1653 - 1657
(2009/06/28)

Microwave-assisted, rapid, solvent-free aza-michael reaction by perchloric acid impregnated on silica gel
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
experimental part
p. 3982 - 3989
(2009/12/24)

Iodine-alumina catalyzed Aza- michael addition under solvent free conditions
An efficient aza-Michael addition of amines to a variety of activated olefins was carried out under solvent free conditions using iodine-alumina as a catalyst at room temperature or under microwave irradiation (in case of solid) in high yield. 2009 Bentham Science Publishers Ltd.
Saikia, Monmi,Kakati, Dwipen,Joseph, Maria Stalin,Sarma, Jadab Chandra
experimental part
p. 654 - 658
(2010/06/15)

Nanocrystalline copper(II) oxide catalyzed aza-Michael reaction and insertion of α-diazo compounds into N-H bonds of amines
Nanocrystalline copper(II) oxide efficiently catalyzed the conjugate addition of aliphatic amines to α,β-unsaturated compounds to produce β-amino compounds with excellent yields under mild reaction conditions. Similarly, Glycine esters are obtained in good yields by the insertion of α-diazoacetate into N-H bonds of amines. The catalyst is used for three cycles with minimal loss of activity.
Kantam, M. Lakshmi,Laha, Soumi,Yadav, Jagjit,Jha, Shailendra
experimental part
p. 4467 - 4469
(2009/12/01)

An efficient ZrCl4 catalyzed aza-michael addition reaction: Synthesis of C-linked carbo β3-amino acids
A mild aza-Michael protocol has been developed using ZrCl4 as catalyst on α, β-unsaturated esters and nitriles. The aromatic amines were found to give the products with ease. The ZrCl4 mediated route was compatible with acid sensitive carbohydrate esters and provided an efficient method to prepare C-linked carbo β3-amino acids (β3-Caa).
Damera, Krishna,Reddy, Katta L.,Sharma, Gangavaram V.M.
experimental part
p. 151 - 155
(2010/04/23)

Imidazolium-based polymer supported gadolinium triflate as a heterogeneous recyclable Lewis acid catalyst for Michael additions
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
p. 3466 - 3470
(2008/09/21)

N-donor ligand as catalyst: A simple Aza-Michael addition reaction in aqueous media
(Chemical Equation Presented) A novel approach for the Aza-Michael addition reactions between various amines and α,β-unsaturated esters, nitriles and ketones using N-donor Ligand catalyst (3 mol %) is described. The reactions are carried out in aqueous media at an ambient temperature to afford the products in excellent yields.
Pawar, Shivaji S.,Dekhane, Deepak V.,Shingare, Murlidhar S.,Thore, Shivaji N.
experimental part
p. 1869 - 1873
(2009/06/18)

Vanadyl(IV) acetate: An efficient, reusable heterogenous catalyst for Aza-Michael reaction under solvent-free conditions
Vanadyl(IV) acetate [VO(OAc)2] efficiently catalyzes the conjugate addition of aliphatic, aromatic amines to α,β-unsaturated carbonyl compounds in solvent-free media at room temperature to afford corresponding amino compounds in good to excellent yields. The catalyst can be recovered and reused for further cycles. Copyright Taylor & Francis Group, LLC.
Trivedi, Rajiv,Lalitha,Roy, Sarabindu
p. 3556 - 3566
(2008/12/23)

Asymmetric hydroamination of acrylonitrile derivatives catalyzed by Ni(II)-complexes
Chiral ferrocenyl tridentate phosphine ligands were synthesized and used in asymmetric hydroamination reactions catalyzed by Ni(II)-complexes. Compounds of the type [Ni(PPP)L]2+, where L is a chloride, solvent molecule or a coordinated substrate, were isolated. The efficiency of these complexes in asymmetric catalysis was high when aliphatic or aromatic amines were reacted with electron-poor olefins, especially with acrylonitrile derivatives. This hydroamination reaction affords up to 95% enantioselectivity at -80 °C for the addition of morpholine to methacrylonitrile (69% ee at room temperature).
Fadini, Luca,Togni, Antonio
experimental part
p. 2555 - 2562
(2009/04/06)

Bromodimethylsulfonium bromide mediated Michael addition of amines to electron deficient alkenes
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.
p. 3805 - 3808
(2008/02/06)

A basic ionic liquid as catalyst and reaction medium: A rapid and simple procedure for Aza-Michael addition reactions
A fast, mild, and quantitative procedure for Michael addition reactions between various amines and α,β-unsaturated carbonyl compounds and nitriles in the presence of an easily accessible basic ionic liquid - 3-butyl-1-methylimidazolium hydroxide, [bmIm]OH - as both catalyst and reaction medium has been developed. For large-scale reactions the products could be directly distilled from the ionic liquid, allowing the use of organic solvents to be avoided totally. The ionic liquid could be reused at least eight times with consistent activity and was stable during the reaction process. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Xu, Jian-Ming,Wu, Qi,Zhang, Qing-Yi,Zhang, Fu,Lin, Xian-Fu
p. 1798 - 1802
(2008/02/08)

Borax as an efficient metal-free catalyst for hetero-Michael reactions in an aqueous medium
Borax, a naturally occurring material, very efficiently catalyzed the conjugate addition of thiols, dithiols and amines to α,β-unsaturated ketones, nitriles, amides, aldehydes and esters in an aqueous medium to afford the corresponding Michael adducts in good yields at room temperature. Recycling of the catalyst and scaling up of the reactions are important attributes of this catalysis. The reactions of thiols and dithiols were relatively more facile than those of the corresponding amines. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Hussain, Sahid,Bharadwaj, Saitanya K.,Chaudhuri, Mihir K.,Kalita, Harjyoti
p. 374 - 378
(2007/10/03)

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted efficient and versatile aza-Michael addition
A convenient and versatile method was developed for aza-Michael addition using a substoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Various nitrogen nucleophiles were efficiently introduced to α,β-unsaturated carbonyl compounds employing 0.5 equiv of DBU. Furthermore, other heteroatomic nucleophiles could also be introduced successfully under the same reaction conditions.
Yeom, Chang-Eun,Kim, Mi Jeong,Kim, B. Moon
p. 904 - 909
(2007/10/03)

Synthesis and preliminary evaluation of novel analogues of quindolines as potential stabilisers of telomeric G-quadruplex DNA
Telomeric DNA is a potential selective target for cancer therapy since the tumour-associated enzyme telomerase regulates telomere maintenance in most cancer cells. The 3′ single-stranded ends of telomeric DNA can be folded into quadruplex structures by appropriate small molecules. We describe the preparation of a new class of 2,7-disubstituted 10H-indolo[3,2-b]quinolines with enhanced selectivity for the stabilisation of quadruplex DNA compared to duplex DNA, and also the preparation of a key intermediate for the synthesis of trisubstituted quindolines.
Le Sann, Christine,Huddleston, Jonathan,Mann, John
p. 12903 - 12911
(2008/03/27)

[HP(HNCH2CH2)3N]NO3: An efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions
In the presence of a catalytic amount of an azaphosphatrane nitrate salt, amines and thiols react readily with Michael acceptors. The salt is also an efficient promoter for the one pot synthesis of α-amino and α-amidonitriles. By anchoring the salt to Merrifield Resin, a reusable heterogeneous catalyst is obtained for these reactions. Evidence is presented for catalysis being attributable solely to the NO3- ion.
Fetterly, Brandon M.,Jana, Nirmal K.,Verkade, John G.
p. 440 - 456
(2007/10/03)