- Crystal and molecular structure of N,N,N′,N′-tetra(2- nitrilethyl) ethane-1,2-diamine and N-(2-nitrilethyl)benzylamine hydrobromide
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N,N,N′,N′-tetra(2-nitrilethyl) ethane-1,2-diamine and N-(2-nitrilethyl)benzylamine hydrobromide were prepared by the addition reaction of acrylonitrile with corresponding amines, and the two structures were determined by X-ray single crystal diffraction. The two compounds crystallize in monoclinic system, and almost no classical hydrogen bond exists in the two crystal structures.
- Gao,Xu,Xu,Ni,Liu
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Read Online
- TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole
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TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.
- Firouzabadi, Habib,Iranpoor, Naser,Farahi, Soghra
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p. 317 - 323
(2018/02/06)
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- RuO4-mediated oxidation of N-benzylated tertiary amines. Four- And three-membered azacycloalkanes as substrates
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Similarly to N-benzylpiperidine and -pyrrolidine, N-benzylazetidine underwent RuO4-catalyzed oxidation by attack at both types of N-methylene C-H bonds: Endocyclic and exocyclic (benzylic). If the reaction is performed in the presence of cyanide, α-aminon
- Florea, Cristina A.,H?rtopeanu, Anca,Stavarache, Cristina,Petride, Horia
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p. 294 - 307
(2018/11/26)
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- Synthesis and structure-activity relationship study of arylsulfonamides as novel potent H5N1 inhibitors
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H5N1 virus, one subtype of highly pathogenic influenza A virus in human infection, has recently received attention due to its unpredictable and high mortality. In this study, a series of arylsulfonamide derivatives were identified as improved H5N1 inhibitors for the influenza treatment by systematic structure-activity relationship investigation. Among them, the most potent H5N1 inhibitor 3h exhibited excellent antiviral activity against H5N1 virus with EC50 value of 0.006 μM and selectivity index 33543.3. Moreover, the molecular docking of 3h with M2 proton channel protein provides practical way for understanding the inhibition of H5N1 with this kind of compounds.
- Yu, Yongshi,Tang, Qi,Xu, Zhichao,Li, Siliang,Jin, Mengyu,Zhao, Zixuan,Dong, Chune,Wu, Shuwen,Zhou, Hai-Bing
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p. 206 - 216
(2018/10/15)
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- Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts
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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.
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p. 2097 - 2106
(2017/02/26)
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- 3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 00336
(2017/09/27)
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- Synthesis, Characterization and Catalytic Application of MCM 41 Supported Phenanthrolinium Dibromide Catalyst for Aza-Michael Addition Reaction in Aqueous Medium
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Abstract: MCM-41 immobilized phenanthrolinium dibromide (phen-MCM-Br2) was easily prepared and applied as an efficient heterogeneous catalyst for aza-Michael addition of aromatic amines to α,β-unsaturated nitriles and nitro compounds in water. The catalyst was characterized by CHN, TGA, FT-IR, SEM, EDAX, XRD, BET, and TEM. It could be simply recovered and reused several times without significant loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
- Hosseinzadeh, Rahman,Aghili, Nora,Tajbakhsh, Mahmood
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p. 1194 - 1203
(2016/07/06)
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- The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solventfree conditions
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Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.
- Douraki, Saba Mohammadi,Massah, Ahmad Reza
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p. 1346 - 1349
(2015/11/10)
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- The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solvent-free conditions
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Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.
- Douraki, Saba Mohammadi,Massah, Ahmad Reza
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p. 1346 - 1349
(2016/02/26)
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- Chemoselective catalytic conjugate addition of alcohols over amines
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A highly chemoselective conjugate addition of alcohols in the presence of amines is described. The cooperative nature of the catalyst enabled chemoselective activation of alcohols over amines, allowing the conjugate addition to soft Lewis basic α,β-unsaturated nitriles. Divergent transformation of the nitrile functionality highlights the utility of the present catalysis. The cooperative nature of a copper catalyst enabled the highly chemoselective activation of alcohols in the presence of amines and thus the conjugate addition of the hydroxy group to soft Lewis basic α,β-unsaturated nitriles. The presented method proceeds under proton-transfer conditions, reverses the innate reactivity of the OH and NH groups, and does not require protecting groups. dppe=1,2-bis(diphenylphosphino) ethane, MeSal=3-methylsalicylate. Copyright
- Uesugi, Shuhei,Li, Zhao,Yazaki, Ryo,Ohshima, Takashi
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supporting information
p. 1611 - 1615
(2014/03/21)
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- Chemo/regioselective Aza-Michael additions of amines to conjugate alkenes catalyzed by polystyrene-supported AlCl3
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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
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p. 1712 - 1716
(2013/03/13)
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- Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions
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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
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- Palladium nanoparticles in glycerol: A versatile catalytic system for C-X bond formation and hydrogenation processes
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Palladium nanoparticles stabilised by tris(3-sulfophenyl)phosphine trisodium salt in neat glycerol have been synthesised and fully characterised, starting from both Pd(II) and Pd(0) species. The versatility of this innovative catalytic colloidal solution has been proved by its efficient application in C-X bond formation processes (X=C, N, P, S) and C-C multiple bond hydrogenation reactions. The catalytic glycerol phase could be recycled more than ten times, preserving its activity and selectivity. The scope of each of these processes has demonstrated the power of the as-prepared catalyst, isolating the corresponding expected products in yields higher than 90%. The dual catalytic behaviour of this glycerol phase, associated to the metallic nanocatalysts used in wet medium (molecular- and surface-like behaviour), has allowed attractive applications in one-pot multi-step transformations catalysed by palladium, such as C-C coupling followed by hydrogenation, without isolation of intermediates using only one catalytic precursor. Copyright
- Chahdoura, Faouzi,Pradel, Christian,Gomez, Montserrat
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supporting information
p. 3648 - 3660
(2014/01/06)
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- O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions
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The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and ,-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Brnsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
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p. 758 - 767
(2013/01/15)
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- Selective and nonselective aza-michael additions catalyzed by a chiral zirconium bis-diketiminate complex
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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
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p. 6986 - 6995
(2014/01/06)
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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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- An efficient biomaterial supported bifunctional organocatalyst (ES-SO 3- C5H5NH+) for the synthesis of β-amino carbonyls
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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
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experimental part
p. 2314 - 2318
(2011/05/02)
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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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- Graphene oxide: An efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes
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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.
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supporting information; experimental part
p. 12673 - 12675
(2012/01/05)
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- Hydroamination and alcoholysis of acrylonitrile promoted by the pincer complex {κP,κC,κP-2,6- (Ph2PO)2C6H3}Ni(OSO 2CF3)
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This report describes the catalytic activity of the pincer-type complex {κP,κC,κP-2,6-(Ph 2PO)2C6H3}Ni(OSO2CF 3) (1) in the anti-Markovnikov addition of aliphatic and aromatic amines and alcohols to acrylonitrile, crotonitrile, and methacrylonitrile. The influence of additives on the catalytic activities was investigated, and it was found that substoichiometric quantities of water promoted the C-N bond forming reactions catalyzed by 1, especially the reactions involving aromatic amines; in comparison, NEt3 had a less dramatic impact. The opposite pattern was observed for the alcoholysis of acrylonitrile promoted by 1: water had no beneficial effect on these reactions, while NEt3 proved to be a potent promoter. Another important difference between these reactions is that hydroamination works better with more nucleophilic amines, whereas the alcoholysis reactions work well with ArOH, CF3CH2OH, and ArCH2OH but not at all with the more nucleophilic aliphatic alcohols methanol, ethanol, and 2-propanol. Both hydroamination and alcoholysis proceed much better with acrylonitrile in comparison to its Me-substituted derivatives crotonitrile and methacrylonitrile. Under optimized conditions, precatalyst 1 promotes conjugate additions to acrylonitrile with catalytic turnover numbers of up to 100 (hydroamination) or higher (alcoholysis). Spectroscopic studies have established that the main Ni-containing species in the hydroamination reactions is a cationic adduct in which the olefinic substrate is bound to the Ni center via its nitrile moiety; this binding activates the double bond toward an outer-sphere nucleophilic attack by the amine (Michael addition). The solid-state structures of the cationic nitrile adducts [{κP, κC,κP-2,6-(Ph2PO)2C 6H3}Ni(NCR)][OSO2CF3] (R = Me (2a), CH2CH2N(H)Ph (2e)), which can be regarded as model complexes for the species involved in the hydroamination catalysis, have been elucidated. Also reported are the solid-state structures of the charge-neutral compound {κP,κC,κP-2,6-(i- Pr2PO)2C6H3}Ni(OSO 2CF3) and an octahedral Ni(II) species resulting from the aerobic/hydrolytic oxidation of 1.
- Salah, Abderrahmen B.,Offenstein, Caroline,Zargarian, Davit
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experimental part
p. 5352 - 5364
(2011/12/13)
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- Solid sodium stannate as a high-efficiency superbase catalyst for anti-Markovnikov hydroamination and hydroalkoxylation of electron-deficient olefins under mild conditions
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A solid superbase with H- above 26.5 has been obtained through thermal treatment of sodium stannate hydrate. It was found to be an efficient catalyst for anti-Markovnikov hydroamination and hydroalkoxylation of electron-deficient olefins under mild conditions.
- Zhang, Shuguo,Wei, Yudan,Yin, Shuangfeng,Au, Chak-Tong
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p. 712 - 716
(2013/01/09)
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- 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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experimental part
p. 1730 - 1735
(2010/07/14)
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- An effective aza-michael addition of aromatic amines to electron-deficient alkenes in alkaline Al2O3
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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
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experimental part
p. 5373 - 5377
(2010/08/06)
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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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- Iodine-alumina catalyzed Aza- michael addition under solvent free conditions
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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
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experimental part
p. 654 - 658
(2010/06/15)
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- Microwave-assisted, rapid, solvent-free aza-michael reaction by perchloric acid impregnated on silica gel
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Highly efficient solvent-free aza-Michael additions of a variety of amines to,-unsaturated carbonyl compounds under microwave-irradiation conditions catalyzed by perchloric acid impregnated on silica gel (HClO4/SiO2) is reported. The reactions are completed within 2-7min in a microwave oven to produce the corresponding adducts in excellent yields, and the catalyst can be recovered and reused.
- Singh, Surya Prakash,Kumar, T. Vijaya,Chandrasekharam,Giribabu,Reddy, P. Yella
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experimental part
p. 3982 - 3989
(2009/12/24)
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- Synthesis of novel deuterium labelled derivatives of N-alkylated polyamines
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Novel di-, tetra- and octadeuterated derivatives of mono-N-alkylated diaminopropanes, spermidines, spermines, symmetrically bis-N-alkylated spermines and unsymmetrically bis-N-alkylated spermines were synthesized. Deuterium labels were introduced into the RHNCH2CH2CN intermediate either by exchanging the protons next to the nitrile group under basic conditions with D2O-EtOD mixture or/and by reducing the nitrile group to a CD2-NH2 fragment with LiAlD4.
- H?kkinen, Merja R.,Kein?nen, Tuomo A.,Khomutov, Alex R.,Auriola, Seppo,Weisell, Janne,Alhonen, Leena,J?nne, Juhani,Veps?l?inen, Jouko
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experimental part
p. 547 - 562
(2009/04/07)
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- Nanocrystalline copper(II) oxide catalyzed aza-Michael reaction and insertion of α-diazo compounds into N-H bonds of amines
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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
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experimental part
p. 4467 - 4469
(2009/12/01)
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- Michael additions of primary and secondary amines to acrylonitrile catalyzed by lipases
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The present Letter details our findings on the lipase-catalyzed Michael reactions between primary or secondary amines and acrylonitrile. Several lipases were evaluated, and good results were obtained leading to the formation of Michael adducts in shorter reaction times than the uncatalyzed reactions.
- Souza, Rodrigo O.M.A. de,Matos, Lilian M.C.,Gon?alves, Karen M.,Costa, Ingrid C.R.,Babics, Ivelize,Leite, Selma G.F.,Oestreicher,Antunes
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experimental part
p. 2017 - 2018
(2009/07/05)
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- Novel synthesis of 3-aminopropionitriles by ring opening of 2-oxazolidinones with cyanide ion
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Nucleophilic attack of cyanide ion on the 5-position of 2-oxazolidinones in the presence of 18-crown-6 gave 3-aminopropionitriles.
- Taniguchi, Tsuyoshi,Goto, Naoya,Ishibashi, Hiroyuki
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supporting information; experimental part
p. 4857 - 4858
(2009/10/26)
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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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- Vanadyl(IV) acetate: An efficient, reusable heterogenous catalyst for Aza-Michael reaction under solvent-free conditions
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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
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p. 3556 - 3566
(2008/12/23)
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- Samarium(III) triflate catalyzed conjugate addition of amines to electron-deficient alkenes
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Amines undergo smooth nucleophilic addition to α,β-unsaturated compounds in the presence of a catalytic amount of samarium(III) triflate at ambient temperature to produce the corresponding β-amino compounds in excellent yields. This method is simple, convenient, and works efficiently under mild conditions. Georg Thieme Verlag Stuttgart.
- Yadav,Ramesh Reddy,Gopal Rao,Narsaiah,Subba Reddy
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p. 3447 - 3450
(2008/09/19)
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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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- Cadmium chloride (CdCl2): An efficient catalyst for conjugate addition of amines to electron-poor alkenes
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Electron-deficient olefins undergo rapid Aza-Michael reaction with a wide range of amines catalyzed by cadmium chloride at room temperature. Copyright Taylor & Francis Group, LLC.
- Vijender, Medamoni,Kishore,Satyanarayana
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p. 591 - 594
(2007/10/03)
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- Borax as an efficient metal-free catalyst for hetero-Michael reactions in an aqueous medium
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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
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p. 374 - 378
(2007/10/03)
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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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- 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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- 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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- 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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- Anti-Markovnikov N-H and O-H additions to electron-deficient olefins catalyzed by well-defined Cu(I) anilido, ethoxide, and phenoxide systems
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The monomeric Cu(I) complexes (IPr)Cu(Z) (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, Z = NHPh, OEt, or OPh) react with YH (Y = PhNH, PhCH2NH, EtO, or PhO) to catalytically add Y-H bonds across the C=C bond of electron-deficient olefins to yield anti-Markovnikov organic products. Catalytic activity has been observed for olefins CH2C(H)(X) with X = CN, C(O)Me, or CO2Me as well as crotononitrile. Preliminary studies implicate an intermediate in which the C-Y bond forms through a nucleophilic addition pathway. Copyright
- Munro-Leighton, Colleen,Blue, Elizabeth D.,Gunnoe, T. Brent
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p. 1446 - 1447
(2007/10/03)
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- Synthesis and antibacterial evaluation of ureides of Baylis-Hillman derivatives
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The synthesis of several 1-(2-cyano-3-aryl-allyl)-3-aryl-urea(thiourea) constructed from the reaction between allylamines generated from Baylis-Hillman acetates and substituted isocyanates and isothiocyanates has been described. Further, their cyclization in the presence of a base led to the formation of 5-arylmethyl-4-imino-3-aryl-3,4-dihydro-1H-pyrimidin-2-ones. All compounds were tested for their antibacterial activity. Few of the compounds showed superior activity or were equipotent to the standard antibacterial agents.
- Nag, Somnath,Pathak, Richa,Kumar, Manish,Shukla,Batra, Sanjay
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p. 3824 - 3828
(2007/10/03)
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- RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles
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The 1,4-conjugate addition of primary, secondary and aromatic amines, thiols, and carbamate to α,β-unsaturated compounds mediated by a catalytic amount (0.5 mol%) of RuCl3 in poly(ethylene glycol) (PEG) provides the desired β-substituted carbonyls in high yields. In particular, we found that primary aliphatic and aromatic amines produced the single adducts as the sole products in very high yields with RuCl3-PEG. RuCl 3-PEG was readily recycled via solvent precipitation with efficient recyclability as evidenced by high yields. Its properties of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, and efficient recyclability make RuCl3-PEG suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls. Georg Thieme Verlag Stuttgart.
- Zhang, Huaxing,Zhang, Yuhong,Liu, Leifang,Xu, Hailiang,Wang, Yanguang
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p. 2129 - 2136
(2007/10/03)
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- Boric acid: A novel and safe catalyst for aza-Michael reactions in water
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Boric acid efficiently catalyzes the conjugate addition of aliphatic amines to α,β-unsaturated compounds to produce β-amino compounds, with great alacrity and excellent yields, in water under mild conditions. Aromatic amines do not participate effectively in the reaction.
- Chaudhuri, Mihir K.,Hussain, Sahid,Kantam, M. Lakshmi,Neelima
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p. 8329 - 8331
(2007/10/03)
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- Transition-metal-based Lewis acid catalysis of aza-type Michael additions of amines to α,β-unsaturated electrophiles in water
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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
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p. 1522 - 1526
(2007/10/03)
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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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- A green, ionic liquid and quaternary ammonium salt-catalyzed aza-Michael reaction of α,β-ethylenic compounds with amines in water
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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
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p. 183 - 184
(2007/10/03)
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- Efficient Copper-Catalyzed Chemo Selective Conjugate Addition of Aliphatic Amines to α,β-Unsaturated Compounds in Water
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The first environmentally benign, highly efficient, conjugate addition of aliphatic amines to α,β-unsaturated compounds catalyzed by simple copper salts in the green solvent, water is described.
- Xu, Li-Wen,Li, Jing-Wei,Xia, Chun-Gu,Zhou, Shao-Lin,Hu, Xiao-Xue
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p. 2425 - 2427
(2007/10/03)
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- Aza-Michael Reactions in Ionic Liquids. A Facile Synthesis of β-Amino Compounds
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Electron-deficient olefins undergo smoothly aza-Michael reactions with a wide range of amines in ionic liquids in the absence of any acid catalyst to produce the corresponding β-amino compounds in excellent yields with high 1,4-selectivity. The recovered ionic liquids can be reused in subsequent reactions without loss of activity. Owing to the high polarity of ionic liquids, the enones show enhanced reactivity thereby reducing reaction times and improving the yields significantly.
- Yadav,Reddy,Basak,Narsaiah
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p. 988 - 989
(2007/10/03)
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