61077-69-8Relevant academic research and scientific papers
Enantioselective Inverse Electron Demand (3 + 2) Cycloaddition of Palladium-Oxyallyl Enabled by a Hydrogen-Bond-Donating Ligand
Zheng, Yin,Qin, Tianzhu,Zi, Weiwei
supporting information, p. 1038 - 1045 (2021/01/25)
Cycloaddition reactions between oxyallyl cations and alkenes are important transformations for the construction of ring systems. Although (4 + 3) cycloaddition reactions of oxyallyl cations are well-developed, (3 + 2) cycloadditions remain rare, and an as
SEVEN-MEMBERED SULFONAMIDES AS MODULATORS OF RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORγ, NR1F3)
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Page/Page column 59, (2013/05/22)
The invention provides modulators for the orphan nuclear receptor RORγ and methods for treating RORγ mediated diseases by administration of these novel RORγ modulators to a human or a mammal in need thereof. Specifically, the present invention provides compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof as well as pharmaceutical compositions comprising said compounds as an active ingredient.
Silver(I)-catalyzed reaction between pyrazole and propargyl acetates: Stereoselective synthesis of the scorpionate ligands (E)-allyl-gem-dipyrazoles (ADPs)
Bhanuchandra,Kuram, Malleswara Rao,Sahoo, Akhila K.
, p. 11824 - 11834 (2014/01/06)
The reaction between readily accessible pyrazole and propargyl acetates in the presence of Ag(I) catalyst yielded a new class of (E)-allyl-gem-dipyrazole scorpionate ligands: 1-aryl-2-N-pyrazolyl allyl acetates and 1,3-dipyrazolyl-3-arylpropene. The reaction showed broad substrate scope, and various functional and protecting groups were tolerated under the reaction conditions. The palladium(II) scorpionate complex could thus be easily prepared and successfully employed in Suzuki-Miyaura cross-couplings in water.
Synthesis of allenes via gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds
Xu, Cheng-Fu,Xu, Mei,Yang, Liu-Qing,Li, Chuan-Ying
experimental part, p. 3010 - 3016 (2012/05/05)
Functionalized allenes are efficiently synthesized in moderate to high yield from gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds. The user-friendly process could be conducted under mild reaction conditions with easily accessible starting materials.
Gold-catalysed activation of epoxides: Application in the synthesis of bicyclic ketals
Balamurugan, Rengarajan,Kothapalli, Raveendra Babu,Thota, Ganesh Kumar
supporting information; scheme or table, p. 1557 - 1569 (2011/04/25)
Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with Ca≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation experiments were carried out to ascertain the mechanism of the reaction. Sequential activation of epoxide and alkyne moieties by a gold catalyst in acetone as solvent has been achieved. This strategyhas been employed to synthesise bicyclic ketals from epoxy alkynes. Copyright
Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B
Ghosh, Nayan,Nayak, Sanatan,Sahoo, Akhila K.
supporting information; experimental part, p. 500 - 511 (2011/04/17)
A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.
[(NHC)AuI]-catalyzed formation of conjugated enones and enals: An experimental and computational study
Marion, Nicolas,Carlqvist, Peter,Gealageas, Ronan,De Fremont, Pierre,Maseras, Feliu,Nolan, Steven P.
, p. 6437 - 6451 (2008/02/13)
The [(NHC)AuI]-catalyzed (NHC = N-heterocyclic carbene) formation of α,β-unsaturated carbonyl compounds (enones and enals) from propargylic acetates is described. The reactions occur at 60°C in 8 h in the presence of an equimolar mixture of [(NHC)AuCl] and AgSbF6 and produce conjugated enones and enals in high yields. Optimization studies revealed that the reaction is sensitive to the solvent, the NHC, and, to a lesser extent, to the silver salt employed, leading to the use of [(ItBu)AuCl]/ AgSbF6 in THF as an efficient catalytic system. This transformation proved to have a broad scope, enabling the stereoselective formation of (E)-enones and -enals with great structural diversity. The effect of substitution at the propargylic and acetylenic positions has been investigated, as well as the effect of aryl substitution on the formation of cinnamyl ketones. The presence or absence of water in the reaction mixture was found to be crucial. From the same phenylpropargyl acetates, anhydrous conditions led to the formation of indene compounds via a tandem [3,3] sigmatropic rearrangement/intramolecular hydroarylation process, whereas simply adding water to the reaction mixture produced enone derivatives cleanly. Several mechanistic hypotheses, including the hydrolysis of an allenol ester intermediate and SN2′ addition of water, were examined to gain an insight into this transformation. Mechanistic investigations and computational studies support [(NHC)AuOH], produced in situ from [(NHC)AuSbF6] and H 2O, instead of cationic [(NHC)AuSbF6] as the catalytically active species. Based on DFT calculations performed at the B3LYP level of theory, a full catalytic cycle featuring an unprecedented transfer of the OH moiety bound to the gold center to the C≡C bond leading to the formation of a gold-allenolate is proposed.
Synthesis of azide-alkyne fragments for 'click' chemical applications; formation of oligomers from orthogonally protected trialkylsilyl-propargyl azides and propargyl alcohols
Montagnat, Oliver D.,Lessene, Guillaume,Hughes, Andrew B.
, p. 6971 - 6974 (2007/10/03)
A series of orthogonally protected 1,4-disubstituted-1,2,3-triazoles were prepared from the corresponding alkynols and trialkylsilyl-propargyl azides via 1,3-dipolar cycloaddition. These cycloadducts were selectively deprotected and extended in a stepwise fashion via further 'click' reactions to form oligomeric peptidomimetic compounds. This methodology gives access to triazole-based peptidomimetics in a controlled fashion and lays the foundation for a fragment-based approach to drug discovery.
Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes
Zhang, Xiaoxia,Sarkar, Sampa,Larock, Richard C.
, p. 236 - 243 (2007/10/03)
A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by IC1, I 2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes.
Atom-efficient assembly of 1,5-oxygen-bridged medium-sized carbocycles by sequential combination of a ru-catalyzed alkyne-alkene coupling and a Prins-type cyclization
Lopez, Fernando,Castedo, Luis,Mascarenas, Jose L.
, p. 4218 - 4219 (2007/10/03)
Ruthenium-catalyzed coupling of readily accessible 1-trimethylsilyl-1-alkyn-3-ols to allyl ethyl ether followed by in situ ketalization and Lewis-acid induced cyclization affords 1,5-oxygen-bridged eight- and nine-membered carbocycles, products which are
