- Conjugated Bis-Guanidines (CBGs) as β-Diketimine Analogues: Synthesis, Characterization of CBGs/Their Lithium Salts and CBG Li Catalyzed Addition of B?H and TMSCN to Carbonyls
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Herein, we report a range of conjugated bis-guanidines (CBGs) L [L={(ArHN)(ArHN)C=N?C=(NAr)(NHAr)}; Ar=2, 6-Me2 - C6H3, (1), 2, 4, 6-Me3?C6H2, (2), 2, 6-Et2?C6H3
- Peddarao, Thota,Baishya, Ashim,Sarkar, Nabin,Acharya, Rudresh,Nembenna, Sharanappa
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p. 2034 - 2046
(2021/05/27)
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- Multinuclear transition metal-containing polyoxometalates constructed from Nb/W mixed-addendum precursors: synthesis, structures and catalytic performance
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Four new transition metal-containing Nb/W mixed-addendum POM trimers with the formula H19[M4(H2O)x(P2W15Nb3O62)3]·m(HCOOH)·nH2O (M = Cu,x= 15,m=
- Chen, Xuenian,Li, Na,Li, Shujun,Ma, Yubin,Xiao, Wanru,Zhang, Jie,Zhao, Yue
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supporting information
p. 8690 - 8695
(2021/07/02)
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- Discovery of the First in Vivo Active Inhibitors of the Soluble Epoxide Hydrolase Phosphatase Domain
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The emerging pharmacological target soluble epoxide hydrolase (sEH) is a bifunctional enzyme exhibiting two different catalytic activities that are located in two distinct domains. Although the physiological role of the C-terminal hydrolase domain is well-investigated, little is known about its phosphatase activity, located in the N-terminal phosphatase domain of sEH (sEH-P). Herein we report the discovery and optimization of the first inhibitor of human and rat sEH-P that is applicable in vivo. X-ray structure analysis of the sEH phosphatase domain complexed with an inhibitor provides insights in the molecular basis of small-molecule sEH-P inhibition and helps to rationalize the structure-activity relationships. 4-(4-(3,4-Dichlorophenyl)-5-phenyloxazol-2-yl)butanoic acid (22b, SWE101) has an excellent pharmacokinetic and pharmacodynamic profile in rats and enables the investigation of the physiological and pathophysiological role of sEH-P in vivo.
- Kramer, Jan S.,Woltersdorf, Stefano,Duflot, Thomas,Hiesinger, Kerstin,Lillich, Felix F.,Kn?ll, Felix,Wittmann, Sandra K.,Klingler, Franca-M.,Brunst, Steffen,Chaikuad, Apirat,Morisseau, Christophe,Hammock, Bruce D.,Buccellati, Carola,Sala, Angelo,Rovati, G. Enrico,Leuillier, Matthieu,Fraineau, Sylvain,Rondeaux, Julie,Hernandez-Olmos, Victor,Heering, Jan,Merk, Daniel,Pogoryelov, Denys,Steinhilber, Dieter,Knapp, Stefan,Bellien, Jeremy,Proschak, Ewgenij
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p. 8443 - 8460
(2019/10/16)
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- Supported Ionic Liquid-Like Phases (SILLPs) as Immobilised Catalysts for the Multistep and Multicatalytic Continuous Flow Synthesis of Chiral Cyanohydrins
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Supported Ionic Liquid-Like Phases have been found to be efficient organocatalysts for the synthesis of cyanohydrin esters under solvent-free conditions by an “electrophile-nucleophile dual activation” based on hydrogen bond formation. The combination of
- Peris, Edgar,Porcar, Raúl,Burguete, María Isabel,García-Verdugo, Eduardo,Luis, Santiago V.
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p. 1955 - 1962
(2019/03/13)
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- Layered double hydroxides (LDHs): As efficient heterogeneous catalyst for the cyanosilylation of aromatic aldehydes
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We report the first application of Layered Double Hydroxides (LDHs) as efficient and novel heterogeneous catalyst for the cyanosilylation of aldehydes with excellent yields and simple work up. The reaction between different aldehydes with electron-withdra
- Afi, Fahimeh,Mokhtari, Javad,Tahoori, Fatemeh
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- Solvent-free cyanosilylation of aromatic and heteroaryl aldehydes catalyzed by a cationic iron N-heterocyclic carbene complex at ambient temperature under UV irradiation
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The cyanosilylation of aromatic aldehydes and heteroaryl aldehydes with trimethylsilyl cyanide (TMSCN) is efficiently catalyzed by an iron complex of the type {[3-isopropyl-1-(1R-phenylethyl)imidazol-2-ylidene]Fe(CO)2}I (3) in presence of UV li
- Kumar, Dharmendra,Prakasham,Gangwar, Manoj Kumar,Ghosh, Prasenjit
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supporting information
(2019/08/07)
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- Low-valent magnesium(i)-catalyzed cyanosilylation of ketones
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The magnesium(i) complex [(XylNacnac)Mg]2 was employed as a highly efficient catalyst for the cyanosilylation of a variety of ketones with trimethylsilyl cyanide under mild conditions. In contrast to the traditional stoichiometric us
- Wang, Weifan,Luo, Man,Li, Jia,Pullarkat, Sumod A.,Ma, Mengtao
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supporting information
p. 3042 - 3044
(2018/03/28)
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- Method for aldehyde cyanosilylation reaction under conditions of no catalyst or solvent
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The invention discloses a method for an aldehyde cyanosilylation reaction under conditions of no catalyst or solvent. In a glove box, aldehyde and trimethylsilyl cyanide are sequentially added to a nuclear magnetic resonance tube, then, the glove box is m
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Paragraph 0105; 0106; 0107
(2018/11/22)
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- Highly efficient oxidative cleavage of alkenes and cyanosilylation of aldehydes catalysed by magnetically recoverable MIL-101
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The catalytic activity of magnetically recoverable MIL-101 was investigated in the oxidation of alkenes to carboxylic acids and cyanosilylation of aldehydes. MIL-101 was treated with Fe3O4 and the prepared catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, N2 adsorption measurements, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy and inductively coupled plasma analysis. The catalytic active sites in this heterogeneous catalyst are Cr3+ nodes of the MIL-101 framework. This heterogeneous catalyst has the advantages of excellent yields, short reaction times and reusability several times without significant decrease in its initial activity and stability in both oxidation and cyanosilylation reactions. Its magnetic property allows its easy separation using an external magnetic field.
- Nourian, Maryam,Zadehahmadi, Farnaz,Kardanpour, Reihaneh,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj
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- Cationic two-dimensional inorganic networks of antimony oxide hydroxide for Lewis acid catalysis
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We have successfully synthesized a rare example of inorganic layered materials possessing a positive charge, which is well outside the isostructural set of layered double hydroxides. This layered architecture consists of two-dimensional corrugated [Sb2O2(OH)]+ layers with linear α,ω-alkanedisulfonate anions residing in the interlamellar space. This cationic material displays a chemical robustness under highly acidic aqueous conditions (pH = 1). Combining the robust nature and the high density of SbIII sites on the exposed crystal facets, our cationic layered material is an efficient, recyclable catalyst for cyanosilylation of benzaldehyde derivatives with trimethylsilyl cyanide. In addition, the Lewis acidity of the SbIII sites also catalyzes the ketalization of carbonyl groups under "green" solvent-free conditions.
- Yin, Jinlin,Fei, Honghan
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supporting information
p. 4054 - 4058
(2018/03/26)
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- A Stable Porphyrin-Based Porous mog Metal-Organic Framework as an Efficient Solvent-Free Catalyst for C-C Bond Formation
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We herein report the porous 4-fold interpenetrated mog (moganite) metal-organic framework (MOF) [Cd3(tipp)(bpdc)2]·DMA·9H2O (1·Cd; H2tipp = 5,10,15,20-tetrakis(4-(imidazol-1-yl)phenyl)porphyrin, H2bpd
- Jiang, Wei,Yang, Jin,Liu, Ying-Ying,Song, Shu-Yan,Ma, Jian-Fang
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supporting information
p. 3036 - 3043
(2017/03/14)
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- Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications
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Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products. (Figure presented.).
- Zheng, Yu-Cong,Xu, Jian-He,Wang, Hui,Lin, Guo-Qiang,Hong, Ran,Yu, Hui-Lei
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p. 1185 - 1193
(2017/04/13)
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- Preparation method of (S)-chlorophenylglycine methyl ester hydrochloride
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The invention discloses a preparation method of (S)-chlorophenylglycine methyl ester hydrochloride. The preparation method comprises the following steps: 1) adding a mixture of o-chlorobenzaldehyde and trimethylsilyl cyanide into a reaction flask, then ad
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Paragraph 0005; 0007
(2017/08/29)
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- Synthesis and reduction of α-fluoroacetonitriles
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A scalable approach for the cyanosilation of benzaldehydes and acetophenones using indium trichloride, a versatile, user friendly catalyst is developed. Cyanohydrin trimethylsilyl ethers are converted in the same pot to α-fluorophenyl acetonitriles which
- Shewalkar, Mukesh P.,Reddy, B. Veera Bhadra,Shinde, Devanand B.
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p. 222 - 226
(2015/06/23)
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- Insight into the catalytic properties and applications of metal-organic frameworks in the cyanosilylation of aldehydes
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Here we present a systematic investigation of the cyanosilylation of aldehydes with trimethylsilyl cyanide (TMSCN) by using metal-organic frameworks (MOFs) as catalysts. Four types of thermally stable MOFs (MIL-47 (V), MIL-53 (Al), MIL-101 (Cr), and UiO-6
- Zhang, Zhiguo,Chen, Jingwen,Bao, Zongbi,Chang, Ganggang,Xing, Huabin,Ren, Qilong
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p. 79355 - 79360
(2015/10/05)
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- The application of spontaneous flocculation for the preparation of lanthanide-containing polyoxometalates intercalated layered double hydroxides: highly efficient heterogeneous catalysts for cyanosilylation
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The lanthanide-containing polyoxometalates (POMs) have been intercalated into layered double hydroxides (LDHs) successfully through the spontaneous flocculation method, resulting in the formation of new heterogeneous LDHs–POMs catalysts Mg3Al–L
- Jia, Yueqing,Song, Yu-Fei,Zhao, Shen
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p. 172 - 180
(2020/12/07)
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- Tri-lacunary polyoxometalates of Na8H[PW9O 34] as heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation and the synthesis of benzoxazole derivatives
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We reported for the first time the development of tri-lacunary polyoxometalates (POMs) of Na8H[A-PW9O34] ·7H2O and Na8H[B-PW9O 34]·19H2O (Na-A-PW9 and Na-B-PW 9) as highly selective and efficient heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation of various aldehydes and ketones and the synthesis of benzoxazole derivatives at 25 C under mild conditions. Since both Na-A-PW9 and Na-B-PW9 display no characteristic porosity, it is proposed that the catalytic reactions proceed not only on the surface and interface, but also in the bulk phase. The catalysts can be easily recovered and reused for at least six times without obvious decrease of catalytic activities and the structures of the catalysts remain unchanged after recycling. The easy preparation, high efficiency, reusability of the heterogeneous catalysts of Na-A-PW9 and Na-B-PW9 exhibit great potential for further application.
- Zhao, Shen,Chen, Yang,Song, Yu-Fei
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p. 140 - 146
(2014/03/21)
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- Neutral π-nucleophile-catalyzed cyanation of aldehydes and ketones
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1-Methoxy-2-methyl-1-(trimethylsiloxy)propene, a neutral π-nucleophile, was found to be able to efficiently catalyze the cyanation (cyanosilylation and cyanocarbonation) of various aldehydes and ketones, and this study provided the first illustration of u
- Wang, Xiu,Tian, Shi-Kai
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p. 1416 - 1420
(2008/03/11)
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- Lithium chloride: An active and simple catalyst for cyanosilylation of aldehydes and ketones
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LiCl acts as a highly effective catalyst for cyanosilylation of various aldehydes and ketones to the corresponding silylated cyanohydrins. The reaction proceeds smoothly with a substrate/catalyst molar ratio of 100-100 000 at 20-25 °C under solvent-free conditions. α,β-Unsaturated aldehydes are completely converted to the 1,2-adducts. The cyanation products can be isolated by direct distillation of the reaction mixture.
- Kurono, Nobuhito,Yamaguchi, Masayo,Suzuki, Ken,Ohkuma, Takeshi
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p. 6530 - 6532
(2007/10/03)
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- Dodecatungestophosphoric acid (H3PW12O40) as a solid green Br?nsted acid catalyzes high yielding and efficient trimethylcyanosylilation reactions of aldehydes and ketones by trimethylsilyl cyanide
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An efficient solvent-free method is described for the addition of TMSCN to carbonyl groups employing dodecatungestophosphoric acid (H3PW 12O40) as a heterogeneous and environmentally benign catalyst. By this method, aromat
- Firouzabadi, Habib,Iranpoor, Nasser,Jafari, Abbas Ali
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p. 1556 - 1559
(2007/10/03)
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- Asymmetric cyanosilylation of aldehydes catalyzed by novel organocatalysts
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A novel proline-based N,N′-dioxide, which is easily prepared from inexpensive chemicals, serves as an effective catalyst for enantioselective cyanosilylation of aldehydes in up to 73% ee. Georg Thieme Verlag Stuttgart.
- Wen, Yuehong,Huang, Xiao,Huang, Jinglun,Xiong, Yan,Qin, Bo,Feng, Xiaoming
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p. 2445 - 2448
(2007/10/03)
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- Solvent-free synthesis of cyanohydrin derivatives catalysed by triethylamine
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A very simple one-step environmentally friendly procedure for the synthesis of O-substituted cyanohydrins from aldehydes and ketones, in the absence of solvent, employing minimum amounts of the corresponding cyanides has been optimised. Aldehydes react more rapidly than ketones using triethylamine as catalyst offering in both cases almost quantitative yields of the corresponding O-trimethylsilyl, O-methoxycarbonyl, O-benzoyl and O-acetyl cyanohydrins. Georg Thieme Verlag Stuttgart.
- Baeza, Alejandro,Najera, Carmen,Retamosa, Ma. De Gracia,Sansano, Jose M.
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p. 2787 - 2797
(2007/10/03)
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- Inorganic/organic salts as heterogeneous basic catalysts for cyanosilylation of carbonyl compounds
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The addition of TMSCN to carbonyl compounds catalyzed by K 2CO3 as heterogeneous catalyst gave the corresponding cyanohydrin trimethylsilyl ethers from 20 minutes to 24 hours with 62% to 99% yields without solvent at room temperature
- He, Bin,Li, Yan,Feng, Xiaoming,Zhang, Guolin
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p. 1776 - 1778
(2007/10/03)
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- Imidazolinium-carbodithioate zwitterions as organocatalysts for the cyanosilylation of aldehydes
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Imidazolinium-carbodithioates as new organocatalysts have been found to catalyze the cyanosilylation of aldehydes in 100% conversion and good yields. The catalysts could be easily recovered during flash column chromatography.
- Blanrue, Amélie,Wilhelm, René
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p. 2621 - 2623
(2007/10/03)
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- Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation
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A class of imidazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II STR1 wherein R1 is selected from lower alkyl, lower haloalkyl, lower hydroxyalkyl, lower aralkenyl, lower aryloxyalkyl, lower arylthioalkyl and heteroaryl; wherein R3 is selected from lower alkyl and amino; and wherein R4 is one or more radicals selected from hydrido, halo, lower alkyl and lower alkoxy; or where R4 together with the phenyl radical forms naphthyl or benzodioxolyl; provided R1 is not lower alkyl when R3 is methyl and when R4 is hydrido, methyl, methoxy or chloro; or a pharmaceutically-acceptable salt thereof.
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- Towards a rational design for resolving agents. Part V; Substituent effects in the resolution of ephedrine using a series of cyclic phosphoric acids
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The effects of various aromatic substituents in both ephedrine and a cyclic phosphoric acid on the quality of resolution via diastereomeric salt formation are investigated.The diastereoselective synthesis of a novel series of chloro-substituted ephedrines
- Haest, Albertus D. van der,Wynberg, Hans,Leusen, Frank, J. J.,Bruggink, Alle
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p. 230 - 235
(2007/10/02)
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- Enzymatic Preparation of Optically Active Cyanohydrin Acetates
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A series of cyanohydrin acetates (1)-(47) of widely varying structures, potential chiral building blocks for numerous synthetic applications, has been prepared in good chemical and often high optical yields by enzymatic hydrolysis of their racemic acetates in the presence of an ester hydrolase from Pseudomonas sp.
- Almsick, Andreas van,Buddrus, Joachim,Hoenicke-Schmidt, Petra,Laumen, Kurt,Schneider, Manfred P.
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p. 1391 - 1393
(2007/10/02)
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- A Convenient One-Pot Cyanosilylation of Aldehydes and Ketones Using Potassium or Sodium Cyanide Impregnated on Amberlite XAD Resin and Trimethylsilyl Chloride
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In the cyanosylilation of benzaldehyde, the combination of potassium or sodium cyanide impregnated on Amberlite XAD resin and trimethylsilyl chloride has been found to be a good one-pot cyanosilylation agent.Although acetonitrile is the best solvent, subs
- Sukata, Kazuaki
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p. 3820 - 3822
(2007/10/02)
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- ASYMMETRIC SYNTHESIS OF α-AMINONITRILES
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The asymmetric synthesis of α-aminonitriles was carried out by the reaction of α-trimethylsilyloxynitriles with optically active α-methylbenzylamine in methanol.The reactions provided moderate yields and good optical purities.
- Mai, Khuong,Patil, Ghanshyam
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p. 1299 - 1304
(2007/10/02)
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- Hypoglycemic 5-substituted oxazolidine-2,4-diones
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Hypoglycemic 5-phenyl and 5-naphthyl oxazolidine-2,4-diones and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; a method of treating hyperglycemic animals therewith; and intermediates useful in the preparation of said compounds.
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- ELECTROPHILIC AMINATION OF ACYL ANION EQUIVALENTS: MILD OXIDATION OF ALDEHYDES TO AMIDES VIA O-(TRIMETHYLSILYL)ALDEHYDE CYANOHYDRIN ANIONS
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The O-(trimethylsilyl)aldehyde cyanohydrin anions 4a-p(1-)*Li(1+) react with 5 to the amines 6.This electrophilic amination corresponds to a mild and specific oxidation of the aldehydes 1a-p to the amides 7a-p.
- Boche, Gernot,Bosold, Ferdinand,Niessner, Manfred
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p. 3255 - 3256
(2007/10/02)
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