- Synthesis and pharmacological evaluation of 3-[(4-Oxo-4H-pyrido[3,2-e][1,3]thiazin-2-yl)(phenyl)amino]propanenitrile derivatives as orally active AMPA receptor antagonists
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In our search for novel orally active α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, we found that conversion of an allyl group in the lead compound 2-[allyl(4-methyl-phenyl)amino]-4H-pyrido[3,2-e][1,3]thiazin-4-one (4)
- Inami, Hiroshi,Shishikura, Jun-ichi,Yasunaga, Tomoyuki,Hirano, Masaaki,Kimura, Takenori,Yamashita, Hiroshi,Ohno, Kazushige,Sakamoto, Shuichi
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- Green synthesis of CuO nanoparticles using: Lantana camara flower extract and their potential catalytic activity towards the aza-Michael reaction
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Aza-Michael addition is one of the most exploited reactions in organic chemistry. It is regarded as one of the most popular and efficient methods for the creation of the carbon-nitrogen bond, which is a key feature of many bioactive molecules. Herein, we report the synthesis of CuO nanoparticles by an alkaline hydrolysis process in the presence of the flower extract of Lantana camara, an invasive weed, followed by calcination in air at 400 °C. Microscopic results indicated that the plant extract played an important role in the modulation of the size and shape of the product. In the presence of extract, porous CuO nanostructures are formed. While mostly aggregated rod-shaped CuO nanostructures are formed in the absence of extract. The products are pure and highly crystalline possessing the monoclinic phase. The CuO nanoparticles have been used as a catalyst in the aza-Michael addition reaction in aqueous medium under ultrasound vibration. The product yield is excellent and the catalyst is reusable up to the fifth cycle. The catalyst system can be extended to various substituted substrates with excellent to moderate yields.
- Chowdhury, Rakesh,Khan, Aslam,Rashid, Md. Harunar
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p. 14374 - 14385
(2020/04/23)
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- 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
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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
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p. 327 - 337
(2017/02/10)
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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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- Copper-Catalyzed Aza-Michael Addition of Aromatic Amines or Aromatic Aza-Heterocycles to α,β-Unsaturated Olefins
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A highly efficient and mild Cu-catalyzed conjugate addition reaction of aromatic amines and aromatic aza-heterocycles to α,β-unsaturated olefins is described. The transformation is promoted by 3-7 mol % of a Cu complex generated in situ from a mixture of inexpensive CuCl, a readily available phosphine or imidazolium salt, and KOt-Bu at ambient temperature. A wide range of β-amino sulfone, β-amino nitrile, and β-amino carbonyl compounds is efficiently and selectively synthesized in high yields (62-99%).
- Kim, Seongcheol,Kang, Seongil,Kim, Gihyeon,Lee, Yunmi
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p. 4048 - 4057
(2016/06/09)
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- Boric acid/glycerol as an efficient catalyst for synthesis of thiomorpholine 1,1-dioxide by double michael addition reaction in water
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Thiomorpholine 1,1-dioxides were prepared with double Michael addition reaction of aromatic amines to divinyl sulfone catalyzed by boric acid/glycerol in water. This catalyst system was also used for the Michael addition reaction of aromatic amines to electron-deficient alkenes. The reaction is simple and green and gives good to excellent yields.
- Halimehjnai, Azim Ziyaei,Hosseyni, Seyedmorteza,Gholami, Hadi,Hashemi, Mohammed M.
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p. 191 - 197,7
(2020/09/02)
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- Ecofriendly and efficient procedure for hetero-Michael addition reactions with an acidic ionic liquid as catalyst and reaction medium
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1-Methylimidazolium trifluoroacetate ([Hmim]-TFA) is reported as a cost-effective catalyst for a simple and environmentally benign hetero-Michael reaction. [Hmim]TFA works both as reaction medium and catalyst. The reaction is applicable to various aromatic sulfur and nitrogen nucleophiles. This method has advantages such as high yields, short reaction time, and simple workup. The catalyst could be recycled several times without any loss of activity.
- Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh,Baghbanzadeh, Mostafa
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experimental part
p. 109 - 112
(2012/06/30)
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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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- Functionalized ionic liquid promoted aza-michael addition of aromatic amines
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A functionalized ionic liquid, 3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulphate ([DDPA][HSO4]) has been used as catalyst for the aza-Michael reactions of aromatic amines with α,β-unsaturated compounds at room temperature to produce β-amino compounds in good yields. The catalyst can be reused for several times without obvious loss of the catalytic activity.
- Liu, Xiao-Bing,Lu, Ming,Lu, Ting-Ting,Gu, Guo-Liang
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experimental part
p. 1221 - 1226
(2011/10/02)
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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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- 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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- 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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- Protonolysis of a toluidinoalkyl platinum(II) complex derived from the insertion of the C=C bond into the Pt-NHR (amido) bond: the role of amine in Pt-catalyzed hydroamination of acrylonitrile
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The complex Pt{2,6-(R2PCH2)2C6H3}(OTf) [R = Ph (1a), Cy (1b)] catalyzes the hydroamination of acrylonitrile with p-toluidine to produce CH2(CN)CH2NH(Tol-p), exclusively. In the catalyzed reactions, platinum intermediates were detected by NMR spectroscopy. The p-tolylamido platinum complex Pt{2,6-(Ph2PCH2)2C6H3}{NH(Tol-p)} (4), containing the pincer ligand, was synthesized from the reaction of 1a and NaNH(Tol-p). Complex 4 reacted with acrylonitrile to yield the regiospecific insertion product Pt{2,6-(Ph2PCH2)2C6H3}{CH(CN)CH2NH(Tol-p)} (5), quantitatively. Reaction of 5 with HX (X = Cl, OTf) generated free acrylonitrile, p-toluidine and Pt{2,6-(Ph2PCH2)2C6H3}X. Reacting 5 with a proton source having a non-coordinating counter anion, [NH3(Tol-p)]BPh4, also produced free acrylonitrile along with a cationic amine complex [Pt{2,6-(Ph2PCH2)2C6H3}{NH2(Tol-p)}]+. On the other hand, reaction of 5 with [NH3(Tol-p)]BPh4 in the presence of excess p-toluidine (ca. 30 equiv.) generated the hydroaminated product CH2(CN)CH2NH(Tol-p), predominantly. Treatment of 5 with [NH2Me2]BPh4 in the absence of amine bases also released the hydroaminated product. These results apparently reveal that the amine substrate plays a critical role in driving the catalytic cycle.
- Seul, Jung Min,Park, Soonheum
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p. 1153 - 1158
(2007/10/03)
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