- Gold-catalyzed partial hydrogenation of activated alkynes mediated by triphenylphosphine
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Gold(I) can exhibit a cooperative effect with triphenylphosphine, accelerating the triphenylphosphine-mediated partial hydrogenation of activated alkynes. In this protocol, 3-arylpropiolates are selectively reduced to the Z -isomer when the aryl ring bears an electron-donor substituent, whereas 3-arylpropynones are reduced to the E-isomers.
- Cocoletzi-Xochitiotzi, Ana Patricia,Hernández-Hernández, Miguel,Medina-Mercado, Ignacio,Jiménez-Martínez, Williams De Jesús,Mastranzo, Virginia Maricela,Porcel, Susana
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supporting information
p. 2379 - 2386
(2020/08/19)
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- Phosphine-mediated partial reduction of alkynes to form both (E)- and (Z)-alkenes
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A mild, phosphine-mediated partial reduction of alkynyl carbonyls to the corresponding alkenes was developed. Tuning of the reaction conditions led to either the (E)- or (Z)-diastereomer with high selectivity. A range of alkynyl esters, amides, and ketones were reduced to form alkenes in good to high yields and with excellent functional group tolerance.
- Pierce, Brett M.,Simpson, Brittany F.,Ferguson, Kane H.,Whittaker, Rachel E.
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supporting information
p. 6659 - 6662
(2018/09/29)
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- Development of new scaffolds as reversible tissue transglutaminase inhibitors, with improved potency or resistance to glutathione addition
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Previous studies within our group have yielded a class of cinnamoyl-based competitive reversible inhibitors for tissue transglutaminase (TG2), with Ki values as low as 1.0 μM (compound CP4d). However, due to the electrophilic nature of their al
- Apperley, Kim Y. P.,Roy, Isabelle,Saucier, Vincent,Brunet-Filion, Nicholas,Piscopo, Sara-Pier,Pardin, Christophe,De Francesco, élise,Hao, Catherine,Keillor, Jeffrey W.
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supporting information
p. 338 - 345
(2017/03/08)
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- Enantioselective synthesis of β-fluoro-β-aryl-α-aminopentenamides by organocatalytic [2,3]-sigmatropic rearrangement
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The tetramisole-promoted catalytic enantioselective [2,3]-sigmatropic rearrangement of quaternary ammonium salts bearing a (Z)-3-fluoro-3-arylprop-2-ene group generates, after addition of benzylamine, a range of β-fluoro-β-aryl-α-aminopentenamides containing a stereogenic tertiary fluorine substituent. Cyclic and acyclic nitrogen substituents as well as various aromatic substituents are tolerated, giving the β-fluoro-β-aryl-α-aminopentenamide products in up to 76% yield, 96:4 dr, and 98:2 er.
- Kasten, Kevin,Slawin, Alexandra M. Z.,Smith, Andrew D.
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supporting information
p. 5182 - 5185
(2017/11/06)
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- Gold-catalyzed Fluorination of Alkynyl Esters and Ketones: Efficient Access to Fluorinated 1,3-Dicarbonyl Compounds
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We developed an efficient synthesis of 2-fluoro-1,3-dicarbonyl compounds using readily available alkynyl ketones or esters as starting material. The key step is the insertion of hydrogen fluoride (HF) to the gold carbene intermediate generated from cationic gold catalyzed addition of N-oxides to alkynyl ketones or esters. This method gives excellent chemical yields and regioselectivity with good functional group tolerance. (Figure presented.).
- Zeng, Xiaojun,Lu, Zhichao,Liu, Shiwen,Hammond, Gerald B.,Xu, Bo
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supporting information
p. 4062 - 4066
(2017/11/30)
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- Preparation of arylpropynamides and their reaction with malonyl acid derivatives
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Synthesis of arylpropynamides and their reactions with different malonic acid derivatives is described. Treatment of arylpropynamides with unsubstituted malonyl chloride furnished N-(3-arylprop-2-ynoyl)-6-chloro-4-hydroxy-2-oxo-2H- pyran-3-carboxamides; m
- Petina, Olgaa. A.,Yakovlev, Igorp. P.,Geffken, Detlef
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p. 803 - 809
(2013/04/10)
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- CHEMICAL COMPOUNDS
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The invention is directed to substituted heteroaryl derivatives. Specifically, the invention is directed to compounds according to Formula Q: wherein D, L, M, W, X, Y, and Z are defined herein. The compounds of the invention are inhibitors of DNA methyltransferase (DNMT) activity - including DNMT1, DNMT3a, or DNMT3b- and are useful in the treatment of cancer and hyperproliferative diseases. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting DNMT activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention
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Page/Page column 116
(2013/05/21)
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- NOVEL 3-HYDROXY-5-ARYLISOXAZOLE DERIVATIVE
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[Problem] To provide a GPR40 activating agent having, as an active ingredient, a novel compound having a GPR40 agonist action, a salt of the compound, a solvate of the salt or the compound, or the like, particularly, an insulin secretagogue and a prophylactic and/or therapeutic agent against diabetes, obesity, or other diseases. [Means of solving the problem] A compound of Formula (I): (where p is 0 to 4; j is 0 to 3; k is 0 to 2; a ring A is a specific cyclic group; a ring B is a benzene ring, a pyridine ring, or a pyrimidine ring; X is —CH2—, O, —S(O)i— (i is 0 to 2), or —NR7—; R1 to R6 are specific groups), a salt of the compound, or a solvate of the salt or the compound.
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Page/Page column 64
(2012/09/10)
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- Preparation of α-bromoacrylates: One-pot procedure for the synthesis of conjugated acetylenic carboxylates from aldehydes with Ph3P/ Br3CCO2Et
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We have established the optimal conditions for the Wittig reaction for synthesizing α-bromoacrylates with a high selectivity, and developed a simple and efficient one-pot procedure for preparing various conjugated acetylenic carboxylates in moderate to high yields. Georg Thieme Verlag Stuttgart.
- Kim, Joong-Gon,Dong, Ho Kang,Doo, Ok Jang
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p. 443 - 447
(2008/04/01)
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- Quinazoline compounds and pharmaceutical compositions containing them
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The use of a compound of formula (I) or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, NH or NR8 where R8 is hydrogen or C1-6alkyl; Ra is a 3-quinoline group or a group of sub-formula (i) where R5, R6 and R7 are various specific organic groups, in the preparation of a medicament for use in the inhibtion of aurora 2 kinase. Novel compounds of formula (I) and pharmaceutical compositions useful in the treatment of cancer are also described and claimed.
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Page/Page column 38
(2008/06/13)
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- Pyrimidine-2,4,6-trione light screening compositions
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The present invention provides compounds of formula I, which are effective in absorbing ultraviolet radiation and can be used as sunscreen agents: wherein R1and R2are each independently C2-C18alkyl, C5/sub
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- Flash Vacuum Pyrolysis of Stabilised Phosphorus Ylides. Part 2. Two-step Conversion of Acid Chlorides into Acetylenic Esters and Terminal Alkynes
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The known thermal extrusion of Ph3PO from α-acyl-α-ethoxycarbonyl ylides 1 to give acetylenic esters 2 can be accomplished in excellent yield by using flash vacuum (FVP) at 500 deg C.Upon rasing the furnace temperature to 750 deg C, this reaction is accompanied by unexpected loss of the ethoxycarbonyl group to give the terminal alkynes 7 in moderate yield.A mechanism is proposed for this reaction based on isotopic labelling studies.Ten new examples of ylides 1 have been prepared for the first time.
- Aitken, R. Alan,Horsburg, Caroline E. R.,McCreadie, J. Graeme,Seth, Shirley
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p. 1727 - 1732
(2007/10/02)
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- Preparation of ethyl arylpropiolates from aryl iodides by palladium-catalyzed cross-coupling reaction
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The palladium-catalyzed cross-coupling reaction of aryl iodides with 3,3,3-triethoxy-1-propyne gave 1-aryl-3,3,3-triethoxy-1-propynes which were converted to the corresponding ethyl arylpropiolates. The arylpropiolates were also synthesized from the cross-coupling reactions of aryl iodides with 2-ethoxycarbonyl-1-ethynylzinc chloride or ethyl (tributylstannyl)propiolate, but the reactions were not generally applicable.
- Sakamoto,Shiga,Yasuhara,Uchiyama,Kondo,Yamanaka
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p. 746 - 748
(2007/10/02)
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- (Ethoxycarbonyliodomethyl)triphenylphosphonium Iodide: A Convenient Reagent for the Direct Synthesis of β-Substituted Propiolic Acids via the Corresponding Esters
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Reaction between (ethoxycarbonyliodomethyl)triphenylphosphonium iodide, potassium carbonate, and various aromatic or aliphatic aldehydes in a liquid solid two phases system gives β-substituted propiolic esters.The corresponding acids are obtained in good yield by hydrolysis.
- Chenault, Jaques,Dupin, Jean-Francois E.
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p. 498 - 499
(2007/10/02)
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- Alkynes from 5-Aminoisoxazoles
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Diazotization of 5-aminoisoxazoles that bear at least one electron-withdrawing group by reaction with sodium nitrite in AcOH-H2O affords substituted acetylenes.A reaction path is proposed.
- Beccalli, Egle M.,Manfredi, Amedea,Marchesini, Alessandro
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p. 2372 - 2375
(2007/10/02)
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- Transmission of substituent effects through extended systems-III. p-Substituted ethyl trans cinnamates and phenylpropiolates
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Infrared data and 13C chemical shifts are reported for a series of ethyl p-substituted trans-cinnamates and ethyl phenylpropiolates.The i.r. values include intensities for the benzene, ethylene and carbonyl vibrations which allow an estimation of resonance effects.The relative importance of the various mechanisms of transmission of substituent effects are discussed and compared to those previously reported for p-substituted trans cinnamonitriles.It is shown that the carbon-carbon triple bond is less efficient in transmitting substituent effects than carbon-carbon double bonds.
- Butt, G.,Topsom, R. D.
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p. 649 - 654
(2007/10/02)
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