- Zirconium(IV) chloride-mediated chemoselective conjugate addition of aliphatic amines to α,β-ethylenic compounds
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Zirconium chloride efficiently catalyzes the conjugate addition of a variety of aliphatic amines to α,β-unsaturated ester, nitriles, and ketones to give the corresponding β-amino derivatives in excellent yields under mild reaction conditions. Aromatic amines do not participate in this transformation. Copyright Taylor & Francis Group, LLC.
- Meshram,Lakshindra,Reddy,Sadashiv,Yadav
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Read Online
- Microwave-induced aza-michael reaction in water: A remarkably simple procedure
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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.
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Read Online
- Heterogeneous Aza-Michael Addition Reaction by the Copper-Based Metal–Organic Framework (CuBTC)
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Abstract: The copper benzene-1, 3, 5-tricarboxylate metal–organic framework (CuBTC) was found to be an effective heterogeneous catalyst for the aza-Michael addition reaction of the four types of amines to electron deficient alkenes at room temperature. The catalytic protocol showed high product yields and outstanding chemo selectivity. The cyclic amines (piperidine and pyrrolidine) and aliphatic amines (n-dibutylamine) provided aza-Michael addition with a high yield of product (?98%) within shorter reaction period (2?h) at room temperature under mild reaction conditions using CuBTC. However, it was observed that the aza-Michael reaction proceeded more slowly, giving 62% yield of product after 24?h in the case of aromatic amine (aniline) with n-butyl acrylate in the presence of CuBTC under identical reaction conditions. The catalyst could be reused four recycles without losing its initial catalytic activity and selectivity. XRD and SEM analysis further confirmed that the crystallinity of catalyst was retained during the reaction. A reaction mechanism is proposed for the aza-Michael addition reaction over heterogeneous CuBTC catalyst. Graphic Abstract: [Figure not available: see fulltext.].
- Bhattacharjee, Samiran,Shaikh, Aftab Ali,Ahn, Wha-Seung
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p. 2011 - 2018
(2020/11/18)
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- Bio-heterogeneous Cu(0)NC@PHA for n-aryl/alkylation at room temperature
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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
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- COMPOUNDS USEFUL IN HIV THERAPY
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The invention relates to compounds of Formulas (I), (II) and (III) salts thereof, pharmaceutical compositions thereof, as well as methods of treating, curing or preventing HIV in subjects.
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Page/Page column 44
(2019/05/22)
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- Nickel(II) N-Heterocyclic Carbene Complexes: Versatile Catalysts for C–C, C–S and C–N Coupling Reactions
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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
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supporting information
p. 2547 - 2556
(2017/05/29)
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- NAPHTHYLUREA DERIVATIVES AND MEDICAL APPLICATIONS THEREOF
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The present invention relates to naphthylurea derivatives. Such substances can significantly inhibit VEGFR2 and PDGFR-β receptor tyrosine kinase phosphorylation at nanomolar concentration levels. It is a novel type of tyrosine kinase inhibitors which can be used in the treatment of tyrosine kinase-mediated diseases or symptoms such as malignancies and ocular diseases accompanied with pathologic neovascularization
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Paragraph 0047; 0048-0049
(2016/08/17)
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- Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines
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1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)3Cl2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Δ3-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate α,β-unsaturated iminium ion prior to oxazine formation.
- Mathis, Cheryl L.,Gist, Brandi M.,Frederickson, Conerd K.,Midkiff, Katie M.,Marvin, Christopher C.
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p. 2101 - 2104
(2013/04/24)
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- Synthesis of 3-(2-aminoethyl)-5-hydroxy-1H-pyrazole derivatives
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Treatment of β-keto ester 8 with hydrazines 9a-g gave 1'-substituted tert-butyl 2-(5-hydroxy-1Hpyrazol- 3-yl)ethylcarbamates 10a-e and 2-(5-oxo-2,5-dihydro-1H-pyrazol-3-yl)ethylcarbamates 11f,g. Acidolytic deprotection of 10b,c afforded the corresponding 3-(2-aminoethyl)-5-hydroxy- 1H-pyrazoles 6b,c in good yields. Acylation of 6 gave either the N-acyl compounds 12b,c and 13c, or the N,O-diacyl derivative 14. Next, three N,N-dialkyl analogues 15a,b and 26c were prepared from dimethyl acetone-1,3-dicarboxylate 21 via condensation with hydrazines 9a and 9h followed by hydrolysis of the esters 22a,b, amidation of the carboxylic acids 23a,b, and reduction of the tertiary carboxamides 24a and 25b,c. ARKAT-USA, Inc.
- Groselj, Uros,Kralj, David,Wagger, Jernej,Dahmann, Georg,Stanovnik, Branko,Svete, Jurij
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experimental part
p. 49 - 65
(2012/03/11)
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- Ultrasound-assisted aza-Michael reaction in water: A green procedure
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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.
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experimental part
p. 969 - 973
(2012/05/20)
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- Aza-Michael reactions in water using functionalized ionic liquids as the recyclable catalysts
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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
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experimental part
p. 775 - 781
(2012/06/18)
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- POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS
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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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- Highly efficient procedure for the conjugate addition of amines to electron deficient alkenes
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The novel efficient procedure has been developed for the conjugate addition of amines to electron deficient alkenes. The results showed that the catalyst was very efficient for the reactions with the excellent yields in several minutes. Operational simplicity, without need of any solvent, low cost of the catalyst used, high yields, reusability, excellent chemoselectivity, applicability to large-scale reactions are the key features of this methodology. The article is published in the original.
- Liao, An-Ping,Lan, Ping,Li, Mei,Lan, Li-Hong
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experimental part
p. 225 - 228
(2010/09/04)
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- Aza-michael addition of amines to α,β-unsaturated compounds using molecular iodine as catalyst
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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
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experimental part
p. 2830 - 2836
(2010/11/02)
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- Silicon tetrachloride catalyzed aza-michael addition of amines to conjugated alkenes under solvent-free conditions
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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
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experimental part
p. 379 - 382
(2010/04/03)
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- Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates
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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.
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experimental part
p. 4455 - 4458
(2010/09/20)
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- Highly efficient Michael addition reaction of amines catalyzed by silica-supported aluminum chloride
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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
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experimental part
p. 1109 - 1119
(2009/09/08)
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- Synthesis and preliminary evaluation of novel analogues of quindolines as potential stabilisers of telomeric G-quadruplex DNA
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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
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p. 12903 - 12911
(2008/03/27)
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- Bromodimethylsulfonium bromide mediated Michael addition of amines to electron deficient alkenes
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Bromodimethylsulfonium bromide has been found to be an efficient catalyst for the Michael addition of a wide variety of amines to electron deficient alkenes at room temperature. The protocol is very simple and chemoselective. Aliphatic and benzylic amines undergo conjugate addition within a very short period under solvent-free conditions and provide excellent yields of products.
- Khan, Abu T.,Parvin, Tasneem,Gazi, Sarifuddin,Choudhury, Lokman H.
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p. 3805 - 3808
(2008/02/06)
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- Significant rate acceleration of the aza-Michael reaction in water
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The addition of amines to conjugated alkenes has been carried out in water at room temperature very efficiently without any catalyst. Significant rate acceleration of this reaction is observed in water compared to organic solvents.
- Ranu, Brindaban C.,Banerjee, Subhash
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p. 141 - 143
(2007/10/03)
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- ZrOCl2·8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions
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At room temperature, ZrOCl2·8H2O on montmorillonite K10 efficiently catalyzes conjugate addition of amines to a variety of conjugated alkenes such as α,β-unsaturated carbonyl compounds, carboxylic esters, nitriles and amides under solvent-free conditions. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency.
- Hashemi, Mohammed M.,Eftekhari-Sis, Bagher,Abdollahifar, Amir,Khalili, Behzad
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p. 672 - 677
(2007/10/03)
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- New mustard-linked 2-aryl-bis-benzimidazoles with anti-proliferative activity
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We describe new methodology for the synthesis of symmetric bis-benzimidazoles carrying 2-aryl moieties, including 2-[4-(3′- aminopropoxy)phenyl] and 2-[4-(3′-aminopropanamido)phenyl] substituents, together with the synthesis of novel hybrid molecules comprising bis-benzimidazoles in ester and amide combination with the N-mustard chlorambucil. The in vitro activities of these compounds against five cancer cell lines are also provided. The Royal Society of Chemistry 2006.
- Le Sann, Christine,Baron, Anne,Mann, John,Van Den Berg, Hendrik,Gunaratnam, Mekala,Neidle, Stephen
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p. 1305 - 1312
(2007/10/03)
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- Ceric ammonium nitrate catalyzed aza-Michael addition of aliphatic amines to α,β-unsaturated carbonyl compounds and nitriles in water
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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.
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p. 1549 - 1553
(2007/10/03)
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- Novel tertiary (meth)acrylates having lactone structure, polymers, resist compositions and patterning process
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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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- LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions
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Several primary and secondary amines were added to α,β- unsaturated esters, nitriles, amides, and ketones to give the corresponding saturated amines mediated by solid lithium perchlorate under solvent-free and environmentally friendly conditions at room temperature.
- Azizi, Najmedin,Saidi, Mohammad R.
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p. 383 - 387
(2007/10/03)
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- Synthesis and preliminary use of novel acrylic ester-derived task-specific ionic liquids
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Novel electrophilic alkenes bearing an ionic liquid-type appendage have been prepared and used in Diels-Alder cycloadditions, 1,4-additions, Heck couplings and Stetter reactions; this new type of support allows easy monitoring of the reactions by NMR and MS as well as simple and efficient work-up and isolation procedures.
- Anjaiah, Siddam,Chandrasekhar, Srivari,Grée, René
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p. 569 - 571
(2007/10/03)
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- Chemoselective Michael type addition of aliphatic amines to α,β-ethylenic compounds using bismuth triflate catalyst
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Catalytic amounts of bismuth triflate efficiently catalyse the conjugate addition of aliphatic amines to α,β-ethylenic compounds in acetonitrile under mild conditions. The reaction is chemoselective, as aromatic amines do not participate in the reaction. Further, the catalyst can be easily recovered and reused.
- Varala, Ravi,Alam, M. Mujahid,Adapa, Srinivas R.
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p. 720 - 722
(2007/10/03)
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- Amine compounds, resist compositions and patterning process
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Novel amine compounds having a nitrogen-containing cyclic structure and a hydrating group such as a hydroxy, ether, ester, carbonyl, carbonate group or lactone ring are useful for use in resist compositions for preventing a resist film from thinning and also for enhancing the resolution and focus margin of resist.
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- Motuporamines, anti-invasion and anti-angiogenic alkaloids from the marine sponge Xestospongia exigua (Kirkpatrick): Isolation, structure elucidation, analogue synthesis, and conformational analysis
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Extracts of the sponge Xestospongia exigua collected in Papua New Guinea were positive in a new assay for anti-invasion activity. Bioassay-guided fractionation led to the identification of the three known motuporamines A (1), B (2), and C (3) along with the new motuporamines D (4), E (5), and F (6) and a mixture of G, H, and I (15). Motuporamines A (1), B (2), and C (3) and the mixture of G, H, and I (15) were responsible for the anti-invasion activity of the crude extract. Motuporamine C (3) has also been found to be anti-angiogenic. A series of analogues of the motuporamines have been synthesized and evaluated for anti-invasive activity. These SAR results revealed that a saturated 15-membered cyclic amine fused to the natural motuporamine diamine side chain (13) represented the optimal structure for anti-invasive activity in this family. Single-crystal X-ray diffraction analysis of one of the analogues 20 showed that in the solid state its 16-membered macrocyclic amine fragment adopted the [4444] quadrangular conformation predicted by calculations to be the lowest energy conformation for the corresponding cycloalkane, cyclohexadecane. These data along with literature X-ray data and conformational analysis for derivatives of azacyclotridecane have been used as precedents for predicting the lowest energy ring conformations of other motuporamines. The SAR data from the natural and synthetic motuporamines have been combined with the conformational analyses to provide an outline of the functionality and shape required for activity in this family of alkaloids and to design a new analogue 49 that showed good anti-invasion activity.
- Williams, David E.,Craig, Kyle S.,Patrick, Brian,McHardy, Lianne M.,Van Soest, Rob,Roberge, Michel,Andersen, Raymond J.
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p. 245 - 258
(2007/10/03)
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- Anthraquinone-photocatalysed addition of amines toα,β-unsaturated esters: a novel route to indolizidone, pyrrolizidone and related ring systems
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The indolizidone 9, the pyrrolizidone 14, a mixture of heliotridone 15a and pseudoheliotridone 15b and the lactam 19 have been synthesized in a one-step anthraquinone-photocatalysed reaction of the corresponding amines, piperidine 1, pyrrolidine 10 and morpholine 16, with α,β-unsaturated esters.
- Das, Suresh,Kumar, J. S. Dileep,Shivaramayya, K.,George, M. V.
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p. 1797 - 1800
(2007/10/02)
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- SYNTHESIS OF 3-SUBSTITUTED 4-PIPERIDONES
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It has been shown that the addition of methyl acrylate and acrylonitrile to the pyrrolidine enamines of 1-methyl-, (1S)-α-phenylethyl-, (1S)-sec-butyl, 1,2-dimethyl, and 1,3-dimethyl-4-piperidone results in the formation of 3- or 5-substituted 4-piperidones, depending on the reaction conditions and the structure of the enamine.The formation of a pair of diastereomers of the 3-substituted 4-piperidones in a 1:1 ratio takes place when there is a chiral substituent on the nitrogen atom in the piperidone ring.
- Grishina, G. V.,Potapov, V. M.,Abdulganeeva, S. A.,Ivanova, I. A.
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p. 1197 - 1201
(2007/10/02)
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