32541-58-5Relevant academic research and scientific papers
Synthesis of novel β-functionalized α-oximinoketones via hetero-Michael addition of alcohols and mercaptans to enones
Bernal, Pablo,Tamariz, Joaquín
, p. 2905 - 2909 (2006)
A new methodology has been developed for the preparation of β-alkoxy and β-sulfenyl ketones by hetero-Michael addition of the corresponding alcohols and thiols to enones under acidic and basic conditions. The direct conversion of enones into β-alkoxy and
Carbon-13 NMR Spectra of 1,3-Dioxolanes. II - Determination of α, β and γ Parameters for 2- and 4-Methyl Groups in Stereoisomeric Derivatives by the Pattern Molecule Method
Espinosa, Antonio,Gallo, Miguel A.,Campos, Joaquin,Enterna, Antonio,Camacho, Encarnacion
, p. 108 - 110 (1988)
On the basis of the stereochemistry of the 1,3-dioxolane ring, the molecular pattern method allows the establishment of α, β and γ parameters for the 2-Me and 4-Me substituents.Values of α, β and γ additive parameters for the syn and anti 4-Me group in 2,2,4-trisubstituted-1,3-dioxolanes are proposed.The average values of the α, β and γ effects for the 2-Me and 4-Me groups obtained by the molecular pattern method are consistent with those reported from a multiple linear regression analysis.KEY WORDS 1,3-Dioxolane derivatives 13C NMR shift parameters Pattern molecule method
2-AMINO-1,3,4-THIADIAZINE AND 2-AMINO-1,3,4-OXADIAZINE BASED ANTIFUNGAL AGENTS
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Page/Page column 43, (2017/02/09)
The invention provides a compound which is a diazine of formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt thereof, for use as an antifungal agent: (I) wherein X, N', C', A and E are as defined herein. The invention also provides a compound of Formula (I) as defined herein.
Functionalized α-oximinoketones as building blocks for the construction of imidazoline-based potential chiral auxiliaries
Gutiérrez, Rsuini U.,Rebollar, Araceli,Bautista, Rafael,Pelayo, Vanessa,Várgas, José Luis,Montenegro, Mabel M.,Espinoza-Hicks, Carlos,Ayala, Francisco,Bernal, Pablo M.,Carrasco, Cuauhtemoc,Zepeda, L. Gerardo,Delgado, Francisco,Tamariz, Joaquín
, p. 230 - 246 (2015/03/04)
Functionalized α-oximinoketones with β-alkoxy, β-alkyl, and β-sulfenyl groups were used as efficient synthons for the preparation of chiral 1-acyl-4-imidazolin-2-ones and 1-acylimidazolidin-2-ones. For the preparation of the former heterocycles, α-oximinoketones were transformed into their respective imidazole N-oxides by neutral treatment with a chiral triazine, followed by reaction with acetic or propionic anhydrides to furnish the desired chiral 1-acetyl- or 1-propionyl-4-imidazolin-2-ones in moderate overall yields. Upon palladium hydroxide-catalyzed hydrogenation, these series were converted into their corresponding 1-acylimidazolidin-2-ones in high diastereoisomeric ratios. Thus, these novel chiral 1-acetyl- and 1-propionyl-imidazolidin-2-ones were obtained with a variety of alkyl groups at the C-4 and C-5 positions of the heterocycle, through a three-step methodology, and can be applied as new potential chiral auxiliaries.
Acidic ionic liquid [NMP]H2PO4 as dual solvent-catalyst for synthesis of β-alkoxyketones by the oxa-Michael addition reactions
Guo, Hui,Li, Xia,Wang, Jun-Liang,Jin, Xiao-Han,Lin, Xian-Fu
experimental part, p. 8300 - 8303 (2010/11/05)
Acidic ionic liquid N-methyl-2-pyrrolidonium dihydrogen phosphate [NMP]H2PO4 was prepared and used as efficient catalyst and reaction medium to synthesize β-alkoxyketones by the oxa-Michael addition reactions for the first time. The
The ionic liquid ethyltri-n-butylphosphonium tosylate as solvent for the acid-catalysed hetero-Michael reaction
Karodia, Nazira,Liu, Xihan,Ludley, Petra,Pletsas, Dimitrios,Stevenson, Grace
, p. 11039 - 11043 (2007/10/03)
A new and convenient method for the acid-catalysed Michael addition reactions of alcohols, thiols and amines to methyl vinyl ketone has been developed using the ionic liquid ethyltri-n-butylphosphonium tosylate. The reaction conditions are mild and obviat
Novel amine-catalysed hydroalkoxylation reactions of activated alkenes and alkynes
Murtagh, Julie E.,McCooey, Seamus H.,Connon, Stephen J.
, p. 227 - 229 (2007/10/03)
Substoichiometric loadings of DBU catalyse the efficient 1,4-addition of alcohols and non-nucleophilic amines such as pyrrole to activated alkenes; the application of this methodology in a one-pot synthesis of a natural product, and as a novel strategy for the synthesis of mono-protected 1,3-carbonyl compounds is reported.
Rhodium-catalyzed addition of alcohols to terminal enones
Farnworth, Marc V.,Cross, Michael J.,Louie, Janis
, p. 7441 - 7443 (2007/10/03)
[Rh(COD)(OMe)]2 was found to catalyze the addition of aliphatic and aromatic alcohols with terminal enones to afford β-alkoxyketones in high yields.
Phosphine-catalyzed hydration and hydroalkoxylation of activated olefins: Use of a strong nucleophile to generate a strong base
Stewart, Ian C.,Bergman, Robert G.,Toste, F. Dean
, p. 8696 - 8697 (2007/10/03)
The direct addition of water and a variety of alcohols to activated olefins was observed in the presence of nucleophilic phosphine catalysts. Unlike existing methods, the reactions proceed at room temperature and in the absence of transition metals, or strong acids or bases. The use of simple commercially available catalysts makes this an attractive method for the preparation of β-hydroxy and β-alkoxy substrates, which are prevalent targets and intermediates in organic synthesis. The scope and mechanism of this reaction has been explored, and the compound that acts as the resting state of the catalyst was synthesized independently. Our mechanism also suggests the possibility of extending the scope of this reactivity to other classes of nucleophiles. Copyright
Meerwein-Ponndorf-Verley-Type Reduction of Dicarbonyl Compounds to Hydroxy Carbonyl Compounds and α,β-Unsaturated Carbonyl Compounds to Allylic Alcohols Catalyzed by Zirconocene and Hafnocene Complexes
Nakano, Tatsuya,Umano, Shigetoshi,Kino, Yoshio,Ishii, Yasutaka,Ogawa, Masaya
, p. 3752 - 3757 (2007/10/02)
Group IVA metallocene complexes such as bis(η5-cyclopentadienyl)zirconium dihydrides, Cp2ZrH2 (1), and hafnium dihydrides, Cp2HfH2 (8), catalyze the chemoselective reduction of polycarbonyl compounds to hydroxy carbonyl compounds.For instance, the reduction of keto aldehydes 3-ketobutanal (2g) and 2-phenyl-2-ketoethanal (2h) proceeded selectively at aldehyde group to provide the corresponding hydroxy ketones 3g and 3h in 91percent and 93percent yields, respectively.Under similar conditions, however, cyclohexanediones were easily aromatized to benzenediols.On the other hand, 1 and 8 also catalyze the selective 1,2-reduction of various types of α,β-unsaturated carbonyl compounds, giving the corresponding allylic alcohols in good to excellent yields.Thus, steroidal dicarbonyl compounds, having an enone framework in their molecules Δ4-androstene-3,17-dione (11a) and Δ4-progestene-3,20-dione (11b) were reduced by 1 to 17-hydroxy-Δ4-androsten-3-one (12a) and 20-hydroxy-Δ4-progest-3-one (12b), which are essential human hormones, in 80percent and 67percent yields, respectively.
