- Copper(i)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphites
-
Intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphite diesters proceeded in the presence of Cu(i)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
- Li, Guangzhe,Yu, Guo,Wang, Chengdong,Morita, Taiki,Zhang, Xuhai,Nakamura, Hiroyuki
-
supporting information
p. 113 - 116
(2021/12/29)
-
- NOVEL HISTONE METHYLTRANSFERASE INHIBITORS
-
The present invention relates to novel compounds of formula (I) as defined herein. The compounds are inhibitors of histone methyltransferases of the seven-beta-strand family, in particular of KMT9.
- -
-
Page/Page column 30; 48
(2021/04/01)
-
- 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
-
-
- Deep compositional understanding of TBA: AlCl3 ionic liquid for its applications
-
Chloroaluminate ionic liquids (ILs) have been immensely used as homogeneous catalyst in Friedel-Crafts reaction. We have recently synthesized chloroaluminate ILs by reacting aluminium chloride with a hydrophobic neutral ligand i.e. tributylamine (TBA:AlCl3). The current study elaborates on the investigations of the composition of the ionic liquids at various stages of their formation. The ionic liquids were synthesized using various mole ratios of tributyl amine and aluminium chloride in range of 1:1 to 1:2.3, in presence of an aromatic solvent in a one pot reaction. Various characterization techniques like Mass spectrometry, 27Al Nuclear Magnetic Resonance, 31P Nuclear Magnetic Resonance and Fourier Transform Infrared spectroscopy were used to elucidate the formation of various moieties of the TBA:AlCl3 Ionic Liquid. This study also elaborates on the investigations of the cationic and anionic moieties and their structure-property relationship for various applications. Various Friedel-Crafts reaction of industrial importance were performed using the ionic liquid having (Al2Cl7)?moiety to assess its performance and compared with conventional processes. The synthesized products were characterised by sophisticated analytical techniques like 1H NMR, 13C NMR, FTIR, GC–MS, GC-FID, to name a few. This class of ionic liquids also have importance in various electrochemical applications like aluminium deposition and aluminium batteries.
- Bhakthavatsalam, Vishnupriya,Chandra, Sudeshna,Choudhury, Rudra Prosad,Lande, Sharad V.,Pradhan, Jeevan,Sakhalkar, Mangesh
-
-
- Michael addition reaction catalyzed by imidazolium chloride to protect amino groups and construct medium ring heterocycles
-
An effective approach for amino protection and construction of a seven-membered ring has been developed. The method uses imidazolium chloride to carry out the Michael addition reaction at low temperatures and perform amino deprotection or construction of a seven-membered ring at high temperatures.
- Dai, Zeshu,Li, Dan,Li, Yanwu,Li, Zhiyao,Luo, Wen,Shang, Suqin,Tian, Qingqiang,Wang, Xuetong,Yuan, Jianyong,Zhang, Ying
-
-
- Method for catalyzing amino protection by imidazole hydrochloride
-
The invention provides an amino protection method which realizes multi-substituted amino protection by using imidazole hydrochloric acid as an accelerator to push derivatives of primary amine, secondary amine and acrylamide to perform Michael addition at a relatively low temperature, wherein the imidazole hydrochloric acid promotes a carbon-nitrogen bond to crack back to the derivatives of primaryamine and acrylamide at a high temperature. The method provided by the invention is simple and economical, high in practicability, free of any other catalysts or additives, capable of protecting amino to have good functional group tolerance and excellent yield and purity, short in reaction time, free from harsh reaction conditions and suitable for industrial production.
- -
-
Paragraph 0039-0043
(2019/08/01)
-
- Synthesis of N-Substituted phosphoramidic acid esters as “reverse” fosmidomycin analogues
-
An efficient synthetic pathway to a series of novel “reverse” fosmidomycin analogues has been developed, commencing from substituted benzylamines. In these analogues, the fosmidomycin hydroxamate moiety is reversed and the tetrahedral methylene carbon adjacent to the phosphonate moiety is replaced by a nitrogen atom bearing different benzyl groups. The resulting phosphonate esters were designed as potential antimalarial “pro-drugs”.
- Adeyemi, Christiana M.,Hoppe, Heinrich C.,Isaacs, Michelle,Klein, Rosalyn,Lobb, Kevin A.,Kaye, Perry T.
-
p. 2371 - 2378
(2019/03/23)
-
- Synthesis and Catalytic Application of Mixed Valence Iron (FeII/FeIII)-Based OMS-MIL-100(Fe) as an Efficient Green Catalyst for the aza-Michael Reaction
-
Abstract: In the present study, open metal site iron-based MOF [MIL-100(Fe)], by a solvothermal method with polygonal morphology, are synthesised and then applied as a heterogeneous green catalyst for aza-Michael addition of various amines with α, β-unsaturated compounds. The MIL-100(Fe) was found to be efficient, selective, green and heterogeneous catalyst for the aza-Michael reaction. The proposed catalyst has better recyclability and can be reused six times without apparent loss of activity. Graphical Abstract: [Figure not available: see fulltext.].
- Rostamnia, Sadegh,Alamgholiloo, Hassan
-
p. 2918 - 2928
(2018/07/30)
-
- On-water magnetic NiFe2O4 nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes
-
Here, we have demonstrated the Michael addition of active methylene compounds, aromatic/aliphatic amines, thiols and alcohols to conjugated alkenes using magnetic nano-NiFe2O4 as reusable catalyst in water. Nano-NiFe2O4 efficiently catalyzed the formation of C-C and C-X (X = N, S, O etc.) bond through 1,4-addition reactions.
- Payra, Soumen,Saha, Arijit,Banerjee, Subhash
-
p. 95951 - 95956
(2016/10/25)
-
- Polymer coated magnetically separable organocatalyst for C[sbnd]N bond formation via aza-Michael addition
-
A polyacrylamide coated magnetite (PAM@MNP) catalyst was synthesized by following a two step approach involving the reaction of magnetite (Fe3O4) particles with coupling agent 3-(trimethoxysilyl)propyl methacrylate followed by grafting of acrylamide and subsequent polymerization via surface initiated radical polymerization technique. The synthesized organocatalyst was used for a one-pot aza-Michael addition reaction of amines with electron deficient alkenes to give β-amino carbonyls. The magnetic properties of the synthesized organocatalyst provide it a facile recovery by external magnet which eliminates the problems arising during catalyst separation by conventional filtration.
- Panwar, Vineeta,Ray, Siddharth S.,Jain, Suman L.
-
p. 5026 - 5032
(2016/11/02)
-
- Copper-Catalyzed Aza-Michael Addition of Aromatic Amines or Aromatic Aza-Heterocycles to α,β-Unsaturated Olefins
-
A highly efficient and mild Cu-catalyzed conjugate addition reaction of aromatic amines and aromatic aza-heterocycles to α,β-unsaturated olefins is described. The transformation is promoted by 3-7 mol % of a Cu complex generated in situ from a mixture of inexpensive CuCl, a readily available phosphine or imidazolium salt, and KOt-Bu at ambient temperature. A wide range of β-amino sulfone, β-amino nitrile, and β-amino carbonyl compounds is efficiently and selectively synthesized in high yields (62-99%).
- Kim, Seongcheol,Kang, Seongil,Kim, Gihyeon,Lee, Yunmi
-
p. 4048 - 4057
(2016/06/09)
-
- Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
-
A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.
- Youn, So Won,Kim, Yi Hyun
-
supporting information
p. 6140 - 6143
(2016/12/09)
-
- 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)
-
- Room temperature N-arylation of amino acids and peptides using copper(i) and β-diketone
-
A mild and efficient method for the N-arylation of zwitterionic amino acids, amino acid esters and peptides is described. The procedure provides the first room temperature synthesis of N-arylated amino acids and peptides using CuI as a catalyst, diketone as a ligand, and aryl iodides as coupling partners. The method is equally applicable for using relatively inexpensive aryl bromides as coupling partners at 80 °C. Using this procedure, electronically and sterically diverse aryl halides, containing reactive functional groups were efficiently coupled in good to excellent yields.
- Sharma, Krishna K.,Sharma, Swagat,Kudwal, Anurag,Jain, Rahul
-
supporting information
p. 4637 - 4641
(2015/04/27)
-
- HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines
-
Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
- Xu, Xuefeng,Zhang, Xu,Wang, Zhiqiang,Kong, Manman
-
p. 40950 - 40952
(2015/05/20)
-
- Aza-Michael reaction: Selective mono- versus bis-addition under environmentally-friendly conditions
-
Aza-Michael reactions between primary amines and methyl propenoate have been investigated under environmentally-friendly solventless heterogeneous catalysis in order to obtain the mono- or the bis-adduct. The reaction conditions can be altered so as to maximise the yields of the required product with high selectivity.
- Bosica, Giovanna,Spiteri, Jonathan,Borg, Caroline
-
p. 2449 - 2454
(2014/04/03)
-
- 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)
-
- Boric acid/glycerol as an efficient catalyst for synthesis of thiomorpholine 1,1-dioxide by double michael addition reaction in water
-
Thiomorpholine 1,1-dioxides were prepared with double Michael addition reaction of aromatic amines to divinyl sulfone catalyzed by boric acid/glycerol in water. This catalyst system was also used for the Michael addition reaction of aromatic amines to electron-deficient alkenes. The reaction is simple and green and gives good to excellent yields.
- Halimehjnai, Azim Ziyaei,Hosseyni, Seyedmorteza,Gholami, Hadi,Hashemi, Mohammed M.
-
p. 191 - 197,7
(2020/09/02)
-
- Highly efficient nanocrystalline zirconosilicate catalysts for the aminolysis, alcoholysis, and hydroamination reactions
-
Nanocrystalline zirconosilicates and titanosilicates with MFI framework structure were hydrothermally synthesized by the addition of organosilanes in the synthesis composition of conventional zirconosilicate and titanosilicate materials. Materials were characterized by a complementary combination of X-ray diffraction, nitrogen sorption, scanning/transmission electron microscopy (S/TEM), ammonia temperature-programmed desorption (TPD), Fourier transform infrared (FT-IR) spectroscopy, and ultraviolet-visible (UV-vis) spectroscopic investigations. Nanocrystalline zeolite catalysts of the present study are reusable. They exhibit significantly higher catalytic activities in aminolysis and alcoholysis compared with the hitherto known catalysts. A range of β-amino alcohols/β-alkoxy alcohols with high regioselectivity were synthesized using zirconosilicates. Application of these materials was also extended in the synthesis of aminoesters by the hydroamination reaction of methyl acrylates and amines. Structure activity relationship was explained based on acidity measurements, reactivity of amines/alcohols, and adsorption of reactants on catalysts.
- Kore, Rajkumar,Srivastava, Rajendra,Satpati, Biswarup
-
p. 2891 - 2904
(2014/01/06)
-
- 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)
-
- 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)
-
- Magnetic Nanoparticle-Supported Glutathione as a Sustainable Organocatalyst
-
This invention relates to the use of nano-organocatalysts, and, more specifically, to the use of magnetic nanomaterial-supported organocatalysts. It is an object of the present invention to provide “green” catalysts and protocols. According to one embodiment of the invention, a nano-organocatalyst in the form of a magnetic nanomaterial-supported organocatalyst is provided. According to other embodiments of the invention, glutathione and cysteine are provided as organocatalysts and magnetic nanomaterial-supported glutathione and magnetic nanomaterial-supported cysteine are provided for use as nano-organocatalysts. According to another embodiment of the invention, a method of using a recyclable magnetic nanomaterial-supported organocatalyst using a totally benign aqueous protocol, without using any organic solvent in the reaction or during the workup, is provided. According to a further embodiment of the invention, a recyclable magnetic nanomaterial-supported organocatalyst for various organocatalytic reactions, including but not limited to Paal-Knorr reactions, aza-Michael addition and pyrazole synthesis, is provided.
- -
-
Page/Page column 8-9
(2011/04/14)
-
- Synthesis and characterization of N-substitutional ethylenediamine derivatives
-
N-Substituted and N,N-disubstituted ethylenediamine derivatives were prepared rapidly in aqueous conditions from 30 to 76 % yields, respectively, on a multi-gram scale starting from inexpensive and commercially available starting materials. The steps involved Michael addition, hydrazinolysis and Curtius rearrangements. The highlight of this method lies on its convenience and economy in accessing these intermediates.
- Yao, Ri-Sheng,Jiang, Lai-En,Wu, Sheng-Hua,Deng, Sheng-Song,Yang, Yang
-
experimental part
p. 3792 - 3794
(2012/01/05)
-
- Lithium tetrafluoroborate catalyzed highly efficient inter- and intramolecular aza-Michael addition with aromatic amines
-
Lithium tetrafluoroborate has been demonstrated for the first time to be an efficient catalyst in intermolecular aza-Michael addition aromatic amines to electron deficient alkenes. Suitability of the same catalyst in intramolecular aza-Michael addition leading 2-aryl-2,3-dihydroquinolin-4(1H) ones has also been described.
- Lad,Kulkarni,Desai,Wadgaonkar
-
experimental part
p. 1059 - 1064
(2012/03/11)
-
- 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)
-
- 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)
-
- Squaric acid as an impressive organocatalyst for Michael addition in water
-
A simple, green, and environmentally benign protocol for squaric acid (5 mg) catalyst conjugate addition of aromatic amines and thiols to unsaturated carbonyl compounds in water in good to excellent yields is developed. The advantages of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, green reaction media and efficient recyclability make this organocatalyst suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls under very mild conditions.
- Azizi, Najmadin,Saki, Elham,Edrisi, Mahtab
-
experimental part
p. 973 - 977
(2012/05/20)
-
- (2-Pyridyl)phenyl methanol: A new reagent for metal-free reduction of nitro aromatic compounds
-
As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic compounds. Operating in the presence of methyl acrylate as an aza-Michael acceptor, a domino process involving reduction and conjugate addition steps allows the one pot formation of β-amino esters. The crucial role of the pyridine nucleus in making this purely thermal reactivity of carbinols possible has been shown.
- Giomi, Donatella,Alfini, Renzo,Brandi, Alberto
-
experimental part
p. 167 - 172
(2011/02/27)
-
- Nano-organocatalyst: magnetically retrievable ferrite-anchored glutathione for microwave-assisted Paal-Knorr reaction, aza-Michael addition, and pyrazole synthesis
-
Postsynthetic surface modification of magnetic nanoparticles by glutathione imparts desirable chemical functionality and enables the generation of catalytic sites on the surfaces of ensuing organocatalysts. In this article, we discuss the developments, unique activity, and high selectivity of nano-organocatalysts for microwave-assisted Paal-Knorr reaction, aza-Michael addition, and pyrazole synthesis. Their insoluble character coupled with paramagnetic nature enables easy separation of these nano-catalysts from the reaction mixture using external magnet, which eliminates the requirement of catalyst filtration.
- Polshettiwar, Vivek,Varma, Rajender S.
-
experimental part
p. 1091 - 1097
(2010/03/25)
-
- Functionalized ionic liquid promoted aza-michael addition of aromatic amines
-
A functionalized ionic liquid, 3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulphate ([DDPA][HSO4]) has been used as catalyst for the aza-Michael reactions of aromatic amines with α,β-unsaturated compounds at room temperature to produce β-amino compounds in good yields. The catalyst can be reused for several times without obvious loss of the catalytic activity.
- Liu, Xiao-Bing,Lu, Ming,Lu, Ting-Ting,Gu, Guo-Liang
-
experimental part
p. 1221 - 1226
(2011/10/02)
-
- Solvent free synthesis of some substituted 1,2,4-triazoles using zeolite nay as a reusable solid support and catalyst
-
NaY zeolite has been employed as a solid support and catalyst for the clean and solvent free synthesis of some substituted 1,2,4-triazoles under microwave irradiation. The compounds were characterized on the basis of their elemental analysis and spectral data.
- Rawal, Manish K.,Sitha, Diwaker,Ameta, Rakshit,Chittora, Anil K.,Punjabi, Pinki B.
-
p. 169 - 170
(2013/09/23)
-
- Aza-michael addition of amines to α,β-unsaturated compounds using molecular iodine as catalyst
-
Aza-Michael adducts are obtained in very good yields by the conjugate addition of aliphatic amines to α,β-unsaturated compounds using molecular iodine as catalyst in dichloromethane at room temperature. Aromatic amines were found to be reactive under reflux in toluene.
- Borah, Kalyan Jyoti,Phukan, Mridula,Borah, Ruli
-
experimental part
p. 2830 - 2836
(2010/11/02)
-
- An effective aza-michael addition of aromatic amines to electron-deficient alkenes in alkaline Al2O3
-
Aza-Michael addition of aromatic or aliphatic amines with various electron-deficient alkenes was performed using alkaline Al2O 3 as solid media at room temperature afforded the corresponding Michael addition products in good to excellent yields.The alkaline Al 2O3 can be easily recovered and reused.
- Ai, Xin,Wang, Xin,Liu, Jin-Ming,Ge, Ze-Mei,Cheng, Tie-Ming,Li, Run-Tao
-
experimental part
p. 5373 - 5377
(2010/08/06)
-
- "On-water" conjugate additions of anilines
-
The conjugate addition of anilines onto unsaturated ketones, esters and N-acylpyrroles was investigated. Based on a recently proposed explanation for the phenomenon of on-water catalysis, operationally simple and mild reaction conditions for effecting these addition reactions have been developed. The success of these additions provides further support for the acid-catalysed nature of on-water chemistry.
- Phippen, Christopher B. W.,Beattie, James K.,McErlean, Christopher S. P.
-
supporting information; experimental part
p. 8234 - 8236
(2010/12/20)
-
- Silicon tetrachloride catalyzed aza-michael addition of amines to conjugated alkenes under solvent-free conditions
-
The efficient and very simple conjugate addition of aromatic and aliphatic amines to α,β-unsaturated carbonyl compounds under solvent-free conditions in the presence of catalytic amount of silicon tetrachloride is reported. The reaction of aryl and alkyl amines with different Michael acceptors gave the corresponding Michael adducts with simple catalyst and good to excellent yields. Georg Thieme Verlag Stuttgart New York.
- Azizi, Najmedin,Baghi, Roya,Ghafuri, Hossein,Bolourtchian, Mohammad,Hashemi, Mohammad
-
experimental part
p. 379 - 382
(2010/04/03)
-
- 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)
-
- Solvent-promoted and -controlled Aza-Michael reaction with aromatic amines
-
(Chemical Equation Presented) 1,4-Addition of anilines onto Michael acceptors proceeds easily in specific polar protic solvents, without any promoting agent. According to the solvent and to the electrophile, the selectivity of the reaction can be finely tuned. With methyl acrylate as electrophile, only monoaddition takes place in water, while the diadduct is yielded in hexafluoroisopropyl alcohol (HFIP). The use of methyl vinyl ketone as a partner affords the monoadduct in water, the diadduct in trifluoroethanol (TFE), and the quinoline in HFIP.
- De, Kavita,Legros, Julien,Crousse, Benoit,Bonnet-Delpon, Daniele
-
scheme or table
p. 6260 - 6265
(2009/12/06)
-
- 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)
-
- Assessment and use of two silicon carbide multi-well plates for library synthesis and proteolytic digests using microwave heating
-
The use of two silicon carbide plates is reported for the preparation of three libraries of organic molecules using microwave heating. In addition, a preliminary study has been carried out, showing that one of the plates can also be used in a proteomics setting. Both the 24-position and 48-position plates heated evenly when irradiated with microwave energy. The 48-position plate was used to prepare a library of N-aryl functionalized β-amino esters via an aza-Michael reaction between anilines and Michael acceptors. The 24-position plate was used to prepare a library of biaryls via a Suzuki coupling methodology and a library of 1,4-dihydropyridines via a Hantzsch synthesis. The 48-position plate was also used to perform the proteolytic digestion of insulin chain B by trypsin. The Royal Society of Chemistry 2009.
- Stencel, Lauren M.,Kormos, Chad M.,Avery, Keri B.,Leadbeater, Nicholas E.
-
experimental part
p. 2452 - 2457
(2009/09/26)
-
- Triethylammonium acetate (TEAA): A recyclable inexpensive ionic liquid promotes the chemoselective aza- and thia-Michael reactions
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A new, highly efficient, inexpensive, recyclable, mild, convenient, and green protocol for chemoselective aza/thia-Michael addition reactions of amines/thiols to α,β-unsaturated compounds using triethylammonium acetate (TEAA) ionic liquid was developed. The catalyst can be recycled ten times and obviate the need for toxic and expensive catalysts.
- Verma, Akhilesh K.,Attri, Pankaj,Chopra, Varun,Tiwari, Rakesh K.,Chandra, Ramesh
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experimental part
p. 1041 - 1047
(2009/11/30)
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- A catalytic method for room-temperature Michael additions using 12-tungstophosphoric acid as a reusable catalyst in water
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12-Tungstophosphoric acid (H3PW12O40) has been found to be an efficient and recyclable catalyst in promoting room temperature Michael additions of amines and aryl thiols to α,β- unsaturated esters and acrylonitrile in water to afford the corresponding saturated amines in good to excellent yields. Georg Thieme Verlag Stuttgart.
- Chen, Xiang,She, Jin,Shang, Zhicai,Wu, Jun,Zhang, Peizhi
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experimental part
p. 3931 - 3936
(2009/05/26)
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- Scale-up of microwave-promoted reactions to the multigram level using a sealed-vessel microwave apparatus
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A range of synthetic transformations have been scaled up successfully using a sealed-vessel multimode microwave unit. These include metal-catalyzed couplings, synthesis of heterocycles, reactions under an atmosphere of reactive gas and two-step one-pot procedures. Also, observations have been made along the way that are of use to chemists addressing scale-up of microwave-promoted reactions.
- Bowman, Matthew D.,Schmink, Jason R.,McGowan, Cynthia M.,Kormos, Chad M.,Leadbeater, Nicholas E.
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p. 1078 - 1088
(2013/01/03)
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- Approaches for scale-up of microwave-promoted reactions
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In this report, we look at a range of classes of reaction involving microwave heating and show how different processing techniques can be used to address scale-up needs. We look at both batch and continuous-flow processing. We have shown that when using batch methodologies working using an open reaction vessel offers operational advantages while still giving good yields of desired products. In cases where open-vessel conditions are not amenable or where particularly volatile or toxic reagents are used, parallel sealed vessels can offer an alternative approach. For continuous-flow processing, homogeneity of the reaction mixture is key. When the mixture is homogeneous, it is possible to move from small-scale sealed-vessel conditions to the continuous-flow apparatus without any modification of reaction conditions or loss in product yield. When either the starting materials or the product mixture contains particulate matter, continuous processing can prove a challenge, but reoptimization of reaction conditions as well as reduction of the concentration may allow these difficulties to be overcome.
- Bowman, Matthew D.,Holcomb, Jennifer L.,Kormos, Chad M.,Leadbeater, Nicholas E.,Williams, Victoria A.
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- NOVEL COMPOUNDS
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There is provided a compound of formula (I): processes for the manufacture thereof, pharmaceutical compositions thereof and uses in therapy.
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Page/Page column 121
(2008/06/13)
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- 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted efficient and versatile aza-Michael addition
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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
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p. 904 - 909
(2007/10/03)
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- Use of a scientific microwave apparatus for rapid optimization of reaction conditions in a monomode function and then substrate screening in a multimode function
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Recently, a new apparatus has become available, which aims to bring together in one unit the advantages of a monomode and a multimode microwave device. We have assessed the applicability of the apparatus toward rapid optimization of reaction conditions in a monomode function and then substrate screening in a multimode function. We have also probed the effects of differences in microwave absorptivity of reaction mixtures on the product conversions in screening multiple substrates simultaneously in a multimode microwave apparatus. We find that when the microwave absorptivity of a reaction mixture is dictated by the solvent, there is little effect on the heating profile of varying the substrate in a screening run. However, this is not the case when reactions involving non-microwave absorbant solvents are used. In this case the characteristics of the substrate can affect significantly the outcome of the reaction.
- Leadbeater, Nicholas E.,Schmink, Jason R.
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p. 6764 - 6773
(2008/02/07)
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- Tandem bis-aza-Michael addition reaction of amines in aqueous medium promoted by polystyrenesulfonic acid
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An efficient and environmentally benign tandem bis-aza-Michael addition of amines catalyzed by polystyrenesulfonic acid (PSSA) is described. This operationally simple high yielding microwave assisted synthetic protocol proceeded in water in the absence of any organic solvent.
- Polshettiwar, Vivek,Varma, Rajender S.
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p. 8735 - 8738
(2008/03/18)
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- β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water
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Highly efficient and environmentally benign aza-Michael additions of amines to α,β-unsaturated compounds catalyzed by β-cyclodextrin in water to produce the corresponding β-amino compounds in excellent yields under mild conditions are described. β-Cyclodextrin can be recovered and reused in subsequent reactions without loss of activity.
- Surendra,Krishnaveni, N. Srilakshmi,Sridhar,Rao, K. Rama
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p. 2125 - 2127
(2007/10/03)
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