74667-98-4Relevant academic research and scientific papers
Selective α-Methylation of Ketones
Frolov, Andriy I.,Ostapchuk, Eugeniy N.,Pashenko, Alexander E.,Chuchvera, Yaroslav O.,Rusanov, Eduard B.,Volochnyuk, Dmitriy M.,Ryabukhin, Sergey V.
, p. 7333 - 7346 (2021)
The convenient and scalable preparative approach for the two-step α-methylation of ketones is described. The optimized protocols for regioselective preparation of enaminones with further diastereoselective and functional groups tolerant hydrogenation to α-methylketones are developed. The scope and limitations of the proposed methodology are discussed. The advantages compared to known procedures are demonstrated. The unexpected role of acetone in the hydrogenation is suggested. The evaluation of the method for both early building block synthesis and late-stage CH-functionalization is shown. The elaborate procedures' preparability and scalability are demonstrated by the synthesis of several α-methyl ketones up to 100 g amount.
Directed C-C bond cleavage of a cyclopropane intermediate generated from: N -tosylhydrazones and stable enaminones: Expedient synthesis of functionalized 1,4-ketoaldehydes
Ni, Meiyan,Zhang, Jianguo,Liang, Xiaoyu,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 12286 - 12289 (2017/11/20)
An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from
PYRIDO PYRIMIDINONES, DIHYDRO PYRIMIDO PYRIMIDINONES AND PTERIDINONES USEFUL AS RAF KINASE INHIBITORS
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Page/Page column 105, (2010/11/08)
The present invention provides compounds having the formula: (I) wherein A-B together represents one of the following structures; (II), (III), (IV) and n, R1, R2, R3, R4, L1, L2, Y and Z are as defined in classes and subclasses herein, and pharmaceutical compositions thereof, as described generally and in subclasses herein, which compounds are useful as inhibitors of protein kinase (e.g., RAF), and thus are useful, for example, for the treatment of RAF mediated diseases.
STUDY OF THE ESCHENMOSER SULFIDE CONTRACTION METHOD WITH AND WITHOUT A THIOPHILE
Corsaro, A.,Perrini, G.,Testa, M. G.,Chiacchio, U.
, p. 197 - 206 (2007/10/02)
Results obtained and observations made by applying the title method for the synthesis of enaminones 5a-o, using triphenylphosphine as a thiophile and triethylamine as a base, are reported.The product distributions of the deprotonations of α-phenacylthio iminium bromides with and without thiophile and those known from thiouronium and heterocyclic thionium analogs are compared.Key words: Enaminones; α-phenacylthio iminium bromides; disulfides; thiiranes.
Palladium-Promoted Transformation of β-Amino Ketones to Enaminones
Murahashi, Shun-Ichi,Mitsue, Yo,Tsumiyama, Tatsuo
, p. 3285 - 3290 (2007/10/02)
The reaction of β-amino ketones with bis(acetonitrile)dichloropalladium(II) in the presence of triethylamine gives the corresponding enaminones regioselectively.The cyclic β-amino ketones can be converted into the corresponding exocyclic enaminones.The enaminones thus obtained are versatile synthetic intermediates.The reaction of (E)-enaminones with organocuprates gave the corresponding (E)-α,β-unsaturated ketones.
SYNTHESIS OF ENAMINONES BY Pd(II) INDUCED DEHYDROGENATION OF β-AMINO KETONES
Murahashi, Shun-Ichi,Tsumiyama, Tatsuo,Mitsue, Yo
, p. 1419 - 1422 (2007/10/02)
The reaction of β-amino ketones with bis(acetonitrile)dichloropalladium(II) in the presence of triethylamine gives enaminones regioselectively.
ADDITION OF ORGANOMETALLICS ON α,β-UNSATURATED THIOCARBONYL COMPOUNDS II. MICHAEL ADDITION OF LITHIUM ENOLATES ON THIOAMIDE AND DITHIOCARBAMATE VINYLOGS AND THIOAROYLFORMAMIDINE
Guemas, Jean-Pierre,Lees, Michele,Reliquet, Alain,Villieras, Jean
, p. 325 - 340 (2007/10/02)
α,β-Unsaturated thiocarbonyl compounds substituted by a secondary amino group in position β, such as thioamide vinylogs, thioaroylformamidines react with lithium enolates of esters, ketones or amides to give 1,4-addition compounds.In the presence of magnesium bromide 1,4-adducts undergo an intramolecular cyclization to give 2H-thiopyranones.Methylation of the 1,4-adducts is followed by a stereospecific elimination of the amine and leads to (1-Z)-1,3-dienic carbonyl compounds: with thioamide vinylogs, δ-methylthio-α,β,γ,δ-diethylenic ketones, esters and amides are obtained.Dithiocarbamate vinylogs give the α-ethylenic ketene dithioacetals, with a carbonyl function in δ-position.Substituted dihydrothiophenes and thiazolines are prepared by the reaction of ethyl α-chloro-α-lithiopropionate with aminopropenethione and thioaroylformamidine respectively.
