- Ultrasonic studies of intermolecular interactions in binary mixtures of 4-methoxy benzoin with various solvents: Excess molar functions of ultrasonic parameters at different concentrations and in different solvents
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Density (ρ), ultrasonic velocity (U), for the binary mixtures of 4-methoxy benzoin (4MB) with ethanol, chloroform, acetonitrile, benzene, and di-oxane were measured at 298 K. The solute-solvent interactions and the effect of the polarity of the solvent on
- Thanuja,Nithya,Kanagam, Charles C
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Read Online
- Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement
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α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.
- Li, Ling,Zhang, Shiqi,Deng, Xiongfei,Li, Guangxun,Tang, Zhuo,Zhao, Gang
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supporting information
p. 6819 - 6824
(2021/09/08)
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- Visible Light Enabled Formal Cross Silyl Benzoin Reaction as an Access to α-Hydroxyketones
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In this work, a visible-light enabled coupling of acylsilanes with aldehydes to give a range of cross-benzoin type products α-hydroxyketones is described. The reaction could proceed at ambient temperature, with the irradiation of low energy visible light, and without addition of photosensitizer or any other additives. (Figure presented.).
- Ma, Liyao,Yu, Yinghua,Xin, Luoting,Zhu, Lei,Xia, Jiajin,Ou, Pengcheng,Huang, Xueliang
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supporting information
p. 2573 - 2577
(2021/04/05)
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- UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions
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UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.
- Zheng, Lewei,Huang, Hongli,Yang, Chao,Xia, Wujiong
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supporting information
p. 1034 - 1037
(2015/03/30)
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- Mechanism of α-ketol-type rearrangement of benzoin derivatives under basic conditions
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The mechanism of base-catalyzed rearrangement of ring-substituted benzoins in aqueous methanol was examined by kinetic and product analyses. Substituent effects on the rate and equilibrium constants revealed that the kinetic process has a different electron demand compared to the equilibrium process. Reactions in deuterated solvents showed that the rate of H/D exchange of the α-hydrogen is similar to the overall rate toward the equilibrium state. A proton-inventory experiment using partially deuterated solvents showed a linear dependence of the rate on the deuterium fraction of the solvent, indicating that only one deuterium isotope effect contributes to the overall rate process. All these results point to a mechanism in which the rearrangement is initiated by the rate-determining α-hydrogen abstraction rather than a mechanism with initial hydroxyl hydrogen abstraction as in the general α-ketol rearrangement.
- Karino, Masahiro,Kubouchi, Daiki,Hamaoka, Kazuki,Umeyama, Shintaro,Yamataka, Hiroshi
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p. 7194 - 7198
(2013/08/23)
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- Silicon and silicon oxide surface modification using thiamine-catalyzed benzoin condensations
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The benzoin condensation that involves the umpolung coupling of two aldehyde groups has been applied to the formation of functionalized silicon and silicon oxide surfaces using thiamine and other N-heterocyclic carbene (NHC) catalysis in water. This bioorthogonal conjugation of an aldehyde to a modified silicon or silicon oxide surface has been monitored and characterized using X-ray photoelectron spectroscopy and IR spectroscopy. NHC catalysis was found to be efficient in water mediating full conversion of the aldehyde functionalized silicon oxide surfaces at the interface.
- Hoop, Kelly A.,Kennedy, David C.,Mishki, Trevor,Lopinski, Gregory P.,Pezacki, John Paul
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experimental part
p. 262 - 270
(2012/04/23)
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- An eco-friendly method for synthesis of symmetrical and unsymmetrical benzoin derivatives
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A rapid, highly efficient and mild green synthesis of symmetrical and unsymmetrical benzoin derivatives was achieved from the reaction of benzaldehyde derivatives with potassium cyanide in dimethyl sulfoxide under argon gas and ultrasound. This simple method affords benzoin derivatives at room temperature in short reaction times with high yield and purity.
- Safari, Javad,Arani, Naimeh Moshtael,Isfahani, Anousheh Ramezan
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experimental part
p. 495 - 498
(2011/12/21)
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- Enantioselective aerobic oxidation of α-hydroxy-ketones catalyzed by oxidovanadium(V) methoxides bearing chiral, N-salicylidene- tert -butylglycinates
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Chiral oxidovanadium(V) methoxides prepared from 3,5-disubstituted-N- salicylidene-l-tert-butylglycines and vanadyl sulfate in air-saturated MeOH serve as highly enantioselective catalysts for asymmetric aerobic oxidations and kinetic resolution of alkyl, aryl, and heteroaryl α-hydroxy-ketones with differed α-substituents at ambient temperature in toluene or TBME (tert-butyl methyl ether). The best scenarios involve the use of complexes which bear the tridendate templates derived from 3,5-diphenyl- or 3-o-biphenyl-5-nitro-salicyaldehyde. The kinetic resolution selectivities of the aerobic oxidation process are in the range of 12 to >1000 based on the selectivity factors (krel).
- Chen, Chien-Tien,Kao, Jun-Qi,Salunke, Santosh B.,Lin, Ya-Hui
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supporting information; experimental part
p. 26 - 29
(2011/03/22)
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- Novel, Cyclically Substituted Furopyrimidine Derivatives and Use Thereof
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The present application relates to novel, cyclically substituted furopyrimidine derivatives, methods for their production, their use for the treatment and/or prophylaxis of diseases and their use for the production of medicinal products for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular diseases.
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Page/Page column 20
(2011/06/19)
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- Novel, Acyclically Substituted Furopyrimidine Derivatives and Use Thereof
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The present application relates to novel, acyclically substituted furopyrimidine derivatives, methods for their production, their use for the treatment and/or prophylaxis of diseases and their use for the production of medicinal products for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular diseases.
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Page/Page column 18
(2009/12/28)
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- 2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents
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2,3-Diaryl-5-ethylsulfanylmethyltetrahydrofuran-3-ols were designed and synthesized by the allylations of benzoins followed by iodocyclization and nucleophilic replacement reactions with ethanthiol. These molecules exhibit IC50 for COX-2 at 50 over all the 59 human tumor cell lines at μ M concentration. The Royal Society of Chemistry.
- Singh, Palwinder,Mittal, Anu,Kaur, Satwinderjeet,Holzer, Wolfgang,Kumar, Subodh
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scheme or table
p. 2706 - 2712
(2009/02/03)
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- COMPOUND FOR INHIBITING TYROSINE KINASE ACTIVITY OF DDR2 PROTEIN
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A new furopyrimidine compound, their pharmaceutically acceptable salt, and a tyrosine kinase activity inhibitor. The furopyrimidine compound is a compound defined by chemical formula 1, 2, 3 or 4, on their precursor, and can exist as a form of free base or in an acid-addition salt. Since the furopyrimidine compound has an effect of inhibiting activity of DDR2 tyrosine kinase, it can be used in treating illnesses caused by the DDR2 tyrosine kinase activity such as hepatocirrhosis, rheumatoid arthritis or cancer.
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(2010/02/14)
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- One-pot synthesis of phenytoin analogs
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A series of phenytoin analogs (5,5-diphenylimidazolidine-2,4-dione or 5,5-diphenyl-hydantoin) were synthesized in 65-75% yield from the corresponding substituted benzils. The same products were also obtained directly from α-hydroxy ketones via one-pot procedure.
- Mahmoodi,Emadi
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p. 377 - 382
(2007/10/03)
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- CHEMICAL COMPOUNDS
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Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11betaHSD1 are described
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- Antibody-Catalyzed Benzoin Oxidation as a Mechanistic Probe for Nucleophilic Catalysis by an Active Site Lysine
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Aldolase antibody 24H6, which was obtained by reactive immunization against a 1,3-diketone hapten, is shown to catalyze additional reactions, including H/D exchange and oxidation reactions. Comparison of the H/D exchange reaction at the α-position of a wide range of aldehydes and ketones by 24H6 and by other aldolase antibodies, such as 38C2, pointed at the significantly larger size of the 24H6 active site. This property allowed for the catalysis of the oxidation of substituted benzoins to benzils by potassium ferricyanide. This reaction was used as a mechanistic probe to learn about the initial steps of the 24H6-catalyzed aldol condensation reaction. The Hammett correlation (ρ=4.7) of log(kcat) versus the substituent constant, σ, revealed that the reaction involves rapid formation of a Schiff base intermediate from the ketone and an active site lysine residue. The rate-limiting step in this oxidation reaction is the conversion of the Schiff base to an enamine intermediate. In addition, linear correlation (ρ= 3.13) was found between log(KM) and σ, indicating that electronic rather than steric factors are dominant in the antibody-substrate binding phenomenon and confirming that the reversible formation of a Schiff base intermediate comprises part of the substrate-binding mechanism.
- Sklute, Genia,Oizerowich, Rachel,Shulman, Hagit,Keinan, Ehud
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p. 2159 - 2165
(2007/10/03)
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- Synthesis of 9,10-phenanthrenequinones by photocyclization of derivatives of benzoins: Scope and limitation of the methodology
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Symmetric 9,10-phenanthrenequinones with methyl, methoxy, and chloro substituents at the 3 and 6 positions have been synthesized by photocyclization of 4,5-bis-(aryl)-2-phenyl-1,3,2-dioxaboroles and 2,3- diarydioxenes followed by oxidative hydrolysis.
- Togashi, Denisio Masaharu,Nicodem, David Ernest,Marchiori, Roberto,Marchiori, Maria Luisa P. De F. C.
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p. 1051 - 1063
(2007/10/03)
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- Substituted benzoylbenzene-, biphenyl- and 2-oxazole- alkanoic acid compounds
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There are disclosed substituted benzoylbenzene-, biphenyl- and 2-oxazole- alkanoic acid derivatives and the pharmacologically acceptable salts thereof as inhibitors of PLA2 and lipoxygenase, and their use in the treatment of inflammatory condit
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- Substituted benzoylbenzene-, biphenyl- and 2-oxazole-alkanoic acid derivatives as inhibitors of pla2 and lipoxygenase
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There are disclosed compounds of the formula wherein A is a group having the formula STR1 wherein X is --N-- or STR2 Z is STR3 R1 is hydrogen, lower alkyl or phenyl; R2 is hydrogen or lower alkyl; or R1 and R2 taken together form a benzene ring, with the proviso that when X is --N--, Z is other than STR4 R3 is hydrogen or lower alkyl; n is 1-2; B is STR5 wherein Y is OR5 or N(OH)R8 ; R4 and R5 are each, independently, hydrogen or lower alkyl; R6 is hydrogen, halo or nitro; R7 is STR6 R8 is lower alkyl; m is 0-3; and the pharmacologically acceptable salts thereof, and their use in the treatment of inflammatory conditions, such as rheumatoid arthritis, ulcerative colitis, psoriasis and other immediate hypersensitivity reactions; in the treatment of leukotriene-mediated naso-bronchial obstructive air-passageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like; and as gastric cytoprotective agents.
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- Synthetic, Mechanistic and Photochemical Studies of Phosphate Esters of Substituted Benzoins
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Synthesis of the phosphate esters of several benzoins, variously substituted with methoxy groups in one or both aromatic rings, proceeds via the corresponding cyclic ethylene ketals.These are phosphitylated with bis(2-cyanoethyl) diisopropylphosphoramidit
- Corrie, John E. T.,Trentham, David R.
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p. 2409 - 2418
(2007/10/02)
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- Substituted benzoylbenzene-, biphenyl- and 2-oxazole-alkanoic acid derivatives
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There are disclosed compounds of the formula wherein A is STR1 n is 1-2; B is STR2 wherein R4 and R5 are each, independently, hydrogen or lower alkyl; R6 is hydrogen, halo or nitro; STR3 R8 is lower alkyl; m is
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- CYANOHYDRINS AS SUBSTRATES IN BENZOIN CONDENSATION. REGIOCONTROLLED MIXED BENZOIN CONDENSATION
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O-Benzoylated cyanohydrins of aromatic aldehydes have been used as one of the substrates in the benzoin condensation.They were treated with aromatic aldehydes under phase-transfer conditions to result in benzoin benzoates.By this method aldehydes which fail to undergo condensation using traditional conditions could be converted into benzoins.By the Umpolung of reactivity of the pertinent aldehyde it was possible to prepare both isomeric unsymmetrical benzoins, including the thermodynamically less stable ones.
- Rozwadowska, Maria D.
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p. 3135 - 3140
(2007/10/02)
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- A New Type of P-C and C-C Bond Cleavage Reactions in α-Trimethylsilyloxy-β-oxo Phosphonates and α-Ethoxy-β-oxo Phosphonates. The Synthesis of Unsymmetrical α-Hydroxy Ketones Utilizing 1:1 Carbonyl Adducts of Diethyl Trimethylsilyl Phosphite with Benzaldehyde
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α-Lithiated diethyl α-(trimethylsilyloxy)benzylphosphonate underwent facile acylation with various acylating agents to afford the corresponding α-acylated products in good yields.On treatment with the α-acylated products with 1 M NaOH-EtOH (1:1, v/v) the P-C bond was cleaved with elimination of diethyl phosphate to give α-hydroxy ketones predominantly.On the other hand, when diethyl α-acyl-α-ethoxybenzylphosphonates were treated under the same conditions, they were rather stable and recovered.However, the prolonged alkaline treatment or the use of 4 M NaOH-EtOH (1:1 v/v) resulted in the C-C bond cleavage giving carboxylic acids and diethyl α-ethoxybenzylphosphonate in quantitative yields, respectively.The mechanisms of the above two reactions were proposed and discussed in connection with the Perkow reaction and related reactions.
- Sekine, Mitsuo,Nakajima, Masashi,Hata, Tsujiaki
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p. 218 - 223
(2007/10/02)
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- 2,3-Disubstituted-2,3,5,6,7,8-hexahydro-thiazolo[3,2-a]-[1,3]diazepin-3-ols
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This disclosure describes certain novel 2,3-disubstituted-2,3,5,6,7,8-hexahydro-thiazolo[3,2-][1,3]diazepin-3-ols which are useful as diuretic agents.
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- 2,3-Disubstituted-thiazolo[3,2-a]pyrimidines
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This disclosure describes 2,3-disubstituted-thiazolo[3,2-a]pyrimidines which are useful as diuretic agents.
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