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Fluorescent non-imidazole histamine H3 receptor ligands with nanomolar affinities
ω-Piperidinoalkanamine derivatives with fluorescent moieties (2-cyanoisoindol-1-yl, 7-nitrobenzofurazan-4-yl) have been synthesized starting from piperidine in three steps. The compounds display moderate to good histamine hH3 receptor affinities with Ki values ranging from 178 to 11 nM. The new compounds may act as tools for identification and understanding of the binding site on the histamine H3 receptor.
Amon, Michael,Ligneau, Xavier,Schwartz, Jean-Charles,Stark, Holger
p. 1938 - 1940
(2006)
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Haliclorensin, a novel diamino alkaloid from the marine sponge Haliclona tulearensis
Haliclorensin (1), a novel diamino alkaloid possessing an azacyclodecane ring, has been isolated from the sponge Haliclona tulearensis. Its structure was elucidated on the basis of spectroscopic data, as well as by comparison with γ-amino azacycloalkanes.
Koren-Goldshlager,Kashman,Schleyer
p. 282 - 284
(1998)
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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)

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)

Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts
Herein, we report the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon-heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by -COOH functionality could effectively catalyze the formation of synthetically challenging spiro/glycoquinazolinones under the present reaction conditions.
Majumdar, Biju,Mandani, Sonam,Bhattacharya, Tamalika,Sarma, Daisy,Sarma, Tridib K.
p. 2097 - 2106
(2017/02/26)

A green and convenient approach for the one-pot solvent-free synthesis of coumarins and β-amino carbonyl compounds using Lewis acid grafted sulfonated carbon@titania composite
Abstract: This paper reports an efficient protocol for the synthesis of coumarins via Pechmann reaction, and β-amino carbonyl compounds via aza-Michael reaction using catalytic amount of solid Lewis acid catalyst, C@TiO2–SO3–SbCl2. Six different catalysts were prepared by covalent immobilization of homogeneous Lewis acids onto sulfonated carbon@titania composite derived from amorphous carbon and nano-titania. Among various catalysts tested, C@TiO2–SO3–SbCl2 showed superior catalytic activity. The catalyst could be recycled without significant loss of its catalytic activity and demonstrated versatile catalysis for a wide range of substrates. Graphical abstract: [Figure not available: see fulltext.]
Kour, Manmeet,Paul, Satya
p. 327 - 337
(2017/02/10)

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)

Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions
Iranian dolomite (CaMg(CO3)2) which consists of double-layered carbonates with Ca2+ and Mg2+ ions was utilized as a heterogeneous base catalyst in the CC, CN, and CS bond forming reactions via the Henry, Knoevenagel, aza-Michael, and thia-Michael transformations under mild conditions in water. Iranian dolomite has been characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), Brunauer Emmett Teller (BET) and XRF chemical analysis, while its basic strength was evaluated by following the Hammett indicators procedure. This water-insoluble natural catalyst demonstrated high activity and was reusable.
Tamaddon, Fatemeh,Tayefi, Mohammad,Hosseini, Elaheh,Zare, Elham
p. 36 - 42
(2013/02/22)

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)

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)

Crown ether complex cation ionic liquids: Preparation and applications in organic reactions
A series of crown ether complex cation ionic liquids (CECILs) were designed, synthesised and characterised by NMR spectroscopy, HRMS, thermogravimetric differential thermal analysis (TG-DTA) and elemental analysis. Their applications in various organic reactions were investigated: [15-C-5Na][OH], [15-C-5Na][OAc], [18-C-6K][OH] and [18-C-6K][OAc] (15-C-5=[15]crown-5; 18-C-6=[18]crown-6) efficiently catalysed the Michael addition of alkenes and relevant nucleophiles; [18-C-6K][OH] and [15-C-5Na][OH] effectively catalysed the Henry reaction of nitromethane and aromatic aldehydes; [18-C-6K][OH] has excellent catalytic efficiency for Knoevenagel condensation of aromatic aldehydes and malononitrile; PdCl2/[18-C-6K] 3[PO4]/K2CO3 efficaciously catalysed the Heck reaction of olefins and aromatic halides; [18-C-6K][BrO3] can be used as both oxidant and solvent in the oxidation reaction of aromatic alcohols. The CECIL catalysts [15-C-5Na][OH] (Michael addition) and [18-C-6K][OH] (Henry reaction) can be recycled and reused several times without obvious loss of activity and their recovery is very simple.
Song, Yingying,Jing, Huanwang,Li, Bo,Bai, Dongsheng
experimental part
p. 8731 - 8738
(2011/09/16)

Graphene oxide: An efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes
Graphene oxide was found to be a highly efficient, reusable and cost-effective organocatalyst for the aza-Michael addition of amines to activated alkenes to furnish corresponding β-amino compounds in excellent yields. The Royal Society of Chemistry 2011.
Verma, Sanny,Mungse, Harshal P.,Kumar, Neeraj,Choudhary, Shivani,Jain, Suman L.,Sain, Bir,Khatri, Om P.
supporting information; experimental part
p. 12673 - 12675
(2012/01/05)

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)

An efficient biomaterial supported bifunctional organocatalyst (ES-SO 3- C5H5NH+) for the synthesis of β-amino carbonyls
A biomaterial supported organocatalyst, readily synthesized by the reaction of chemically modified sulfonic group containing expanded corn starch with pyridine exhibited excellent catalytic activity for the synthesis of β-amino carbonyls in excellent yields via aza-Michael addition of amines to electron deficient alkenes. A remarkable enhancement in the reaction rates was observed with the prepared bifunctional organocatalyst in comparison to the either starch grafted sulfonic acid or the corresponding homogeneous pyridinium p-toluenesulfonate.
Verma, Sanny,Jain, Suman L.,Sain, Bir
experimental part
p. 2314 - 2318
(2011/05/02)

Use of protease from Bacillus licheniformis as promiscuous catalyst for organic synthesis: Applications in C-C and C-N bond formation reactions
Commercially available protease from Bacillus licheniformis has been used in different non-conventional biotransformations showing remarkable activity values. The promiscuous behaviour of this enzyme used in the cross-linked enzyme aggregates immobilized form (Alcalase-CLEA), has been successfully demonstrated for the first time in C-C bond formation processes such as aldol, Henry and Mannich reactions. On the other hand, the Bayllis-Hillman reaction between 4-nitrobenzaldehyde and methyl vinyl ketone occurred through unspecific catalysis. Interestingly, aza- Michael addition reactions of secondary amines (diethylamine, piperidine and pyrrolidine) to acrylonitrile have been also efficiently catalyzed, observing with diethylamine the most remarkable differences between the enzyme-mediated reaction and the one in the absence of catalyst. Higher reactivities were attained with pyrrolidine demonstrating the versatility of hydrolases in organic synthesis. Copyright
Lopez-Iglesias, Maria,Busto, Eduardo,Gotor, Vicente,Gotor-Fernandez, Vicente
supporting information; experimental part
p. 2345 - 2353
(2011/10/19)

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)

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.
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(2010/04/23)

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)

Aqueous aza-michael reaction of conjugated alkenes: Toward spermine
An aqueous aza-Michael reaction is efficiently achieved with excellent conversions without any additives. The method works very well on a molar scale with selectively for aliphatic amines. An intermediate for spermine is also made by this green process.
Joshi, Jigar H.,Saiyed, Akeel S.,Bedekar, Ashutosh V.
scheme or table
p. 2857 - 2863
(2010/11/18)

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)

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)

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)

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)

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)

A catalytic method for room-temperature Michael additions using 12-tungstophosphoric acid as a reusable catalyst in water
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
experimental part
p. 3931 - 3936
(2009/05/26)

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)

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)

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)

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)

Significant rate acceleration of the aza-Michael reaction in water
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
p. 141 - 143
(2007/10/03)

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)

Cellulose-supported copper(0) catalyst for aza-Michael addition
Cellulose-supported copper(0) efficiently catalyzes the aza-Michael reaction of N-nucleophiles, such as amines and imidazoles with α,β-unsaturated compounds to produce the corresponding β-amino compounds and N-substituted imidazoles in excellent yields. The reactions are facile and the recovered catalyst is used for several cycles with consistent activity. Georg Thieme Verlag Stuttgart.
Reddy, K. Rajender,Kumar, Nadakudity S.
p. 2246 - 2250
(2007/10/03)

Cerium(IV) ammonium nitrate (CAN) catalyzed aza-Michael addition of amines to α,β-unsaturated electrophiles
Cerium(IV) ammonium nitrate (CAN) catalyzed facile and efficient aza-Michael addition of aromatic and aliphatic amines with α,β-unsaturated electrophiles in the absence of solvent under ultrasound irradiation.
Duan, Zheng,Xuan, Xuejie,Li, Ting,Yang, Chenfei,Wu, Yangjie
p. 5433 - 5436
(2007/10/03)

Ceric ammonium nitrate catalyzed aza-Michael addition of aliphatic amines to α,β-unsaturated carbonyl compounds and nitriles in water
Ceric ammonium nitrate (3 mol%) efficiently catalyzes the aza-Michael reaction of amines with α,β-unsaturated carbonyl compounds in water to produce the corresponding β-amino carbonyl compounds in good to excellent yields (55-99%) for most of the compounds under mild conditions. The reaction is procedurally simple and displays limited chemoselectivity, as aromatic amines were found to be unreactive. Georg Thieme Verlag Stuttgart.
Varala, Ravi,Sreelatha, Nuvula,Adapa, Srinivas R.
p. 1549 - 1553
(2007/10/03)

ZrOCl2·8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions
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
p. 672 - 677
(2007/10/03)

β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water
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
p. 2125 - 2127
(2007/10/03)

Addition of secondary amines to α,β-unsaturated carbonyl compounds and nitrites by using microstructured reactors
Several additions of amines to α,β-unsaturated carbonyl compounds (Michael additions) were performed in a continuous-flow microstructured reactor rig and compared to the respective batch reaction. Dimethylamine/diethylamine/piperidine and acrylic acid ethyl ester/acrylonitrile were employed as two sets of reactants, giving six reactions. Some of these reactions are highly exothermal. Using the traditional batch procedure the olefin must be added quite slowly to the diluted amine to ensure temperature control and safe operation; especially this is necessary for the addition of dimethylamine (40 mass % aqueous solution) to acrylonitrile. Good yields (>85%) are achieved in this way; however, processing time is very long (17-25 h). To reveal the intrinsic kinetic potential and thus to accelerate these reactions, the reactants were mixed in a continuous-flow microstructured reactor rig which allows rapid mixing and efficient removal of the reaction heat. In this way, reaction time was decreased to a few seconds up to about half an hour, which is a change by 2 orders of magnitude. While the yields achieved with the continuous-flow microstructured reactor rig matched those for the batch procedure, the space-time yields for the microflow processing are much higher, in the best case by a factor of about 650.
Loewe,Hessel,Lob,Hubbard
p. 1144 - 1152
(2012/12/23)

Novel tertiary (meth)acrylates having lactone structure, polymers, resist compositions and patterning process
Novel tertiary (meth)acrylate compounds having a lactone structure are polymerizable into polymers having improved transparency, especially at the exposure wavelength of an excimer laser and dry etching resistance. Resist compositions comprising the polymers are sensitive to high-energy radiation, have a high resolution, and lend themselves to micropatterning with electron beams or deep-UV rays.
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(2008/06/13)

RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles
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
p. 2129 - 2136
(2007/10/03)

Cu(acac)2 immobilized in ionic liquids: A recoverable and reusable catalytic system for aza-Michael reactions
Copper(II) acetylacetonate immobilized in ionic liquids efficiently catalyzes the aza-Michael reaction of amines with α,β-unsaturated carbonyl compounds to produce the corresponding β-amino carbonyl compounds with great alacrity in excellent yields. The reactions are far more facile than those reported earlier. The recovered ionic liquid phase containing the copper catalyst can be reused for several cycles with consistent activity.
Kantam, M. Lakshmi,Neeraja,Kavita,Neelima,Chaudhuri, Mihir K.,Hussain, Sahid
p. 763 - 766
(2007/10/03)

Ultrasound-irradiated Michael addition of amines to ferrocenylenones under solvent-free and catalyst-free conditions at room temperature
A facile Michael addition of ferrocenylenones with aliphatic amines under ultrasound irradiation in the absence of solvent and catalyst at room temperature can afford 1-ferrocenyl-3-amino carbonyl compounds rapidly in high yields, which is also efficient in the aza-Michael reaction of other α,β-unsaturated carbonyl compounds such as chalcone, carboxylic ester, etc. However, aromatic amines do not undergo the conjugate addition at all, and the reactions under existing methods do not proceed or take place in low yield after a long reaction time. Apart from experimental simplicity, generality and selectivity, the advantages of this methodology are the rapid, environmentally benign and less expensive processes, which will contribute to the progress of green chemistry.
Yang, Jin-Ming,Ji, Shun-Jun,Gu, Da-Gong,Shen, Zhi-Liang,Wang, Shun-Yi
p. 2989 - 2995
(2007/10/03)

Boric acid: A novel and safe catalyst for aza-Michael reactions in water
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
p. 8329 - 8331
(2007/10/03)

Transition-metal-based Lewis acid catalysis of aza-type Michael additions of amines to α,β-unsaturated electrophiles in water
Several transition-metal-based Lewis acid catalysts, especially FeCl 3 · 7 H2O, CrCl3 · 6 H 2O, and SnCl4 · 4 H2O, were shown to be highly effective for aza-type Michael reactions between electrophilic α,β-unsaturated compounds and both aliphatic and aromatic amines in aqueous solution. Advantages of the new protocol include 1) high-yielding reactions that can be conducted at ambient temperature; 2) the use of inexpensive, stable transition-metal salts as catalysts; and 3) plain H 2O as an environmentally benign solvent.
Xu, Li-Wen,Li, Lyi,Xia, Chun-Gu
p. 1522 - 1526
(2007/10/03)

A green, ionic liquid and quaternary ammonium salt-catalyzed aza-Michael reaction of α,β-ethylenic compounds with amines in water
The first environmentally benign, highly efficient conjugate addition of aliphatic amines to α,β-unsaturated compounds catalysed by simple quaternary ammonium salts and ionic liquids in the green solvent, water, is described.
Xu, Li-Wen,Li, Jing-Wei,Zhou, Shao-Lin,Xia, Chun-Gu
p. 183 - 184
(2007/10/03)

Synthesis of β-amino esters via aza-Michael addition of amines to alkenes promoted on silica: A useful and recyclable surface
A solvent-free protocol for the synthesis of β-amino esters and nitriles has been developed via conjugate addition of amines to electron-deficient alkenes promoted on silica. The silica surface may be recycled. Both aliphatic and aromatic primary or secondary amines worked efficiently to yield the desired adducts in good to excellent yields.
Basu, Basudeb,Das, Pralay,Hossain, Ismail
p. 2630 - 2632
(2007/10/03)