28467-36-9Relevant 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 (2021/06/28)
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.
AMINE-SUBSTITUTED HETEROCYCLIC COMPOUNDS AS EHMT2 INHIBITORS AND METHODS OF USE THEREOF
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Paragraph 0493; 0497-0499, (2018/07/29)
The present disclosure relates to amine-substituted heterocyclic compounds. The present disclosure also relates to pharmaceutical compositions containing these compounds and methods of treating a disorder (e.g., cancer) via inhibition of a methyltransfera
Efficient organocatalytic dual activation strategy for preparing the versatile synthons (2 E)-1-(Het)aryl/styryl-3-(dimethylamino)prop-2-en-1-ones and -(E)-[(dimethylamino)methylene]cycloalkanones
Bindal, Sachin,Kumar, Dinesh,Kommi, Damodara N.,Bhatiya, Sonam,Chakraborti, Asit K.
experimental part, p. 1930 - 1935 (2011/07/31)
A novel organocatalytic dual activation strategy is reported for an efficient synthesis of the versatile synthons (2E)-1-aryl/heteroaryl/styryl-3- (dimethylamino)prop-2-en-1-ones and -(E)-[(dimethylamino)methylene] cycloalkanones. 2-Guanidinoacetic acid (10 mol%) serves as an ambifunctional organocatalyst for the reaction of various aryl/heteroaryl/styryl methyl ketones and cyclic ketones having an -methylene moiety with N,N-dimethylformamide dimethyl acetal at 100 C for 1-3 hours under solvent-free conditions to afford the corresponding (2E)-3-(dimethylamino)prop-2-en-1-ones in 72-95% yields. Georg Thieme Verlag Stuttgart - New York.
A convenient alternative route to β-aminoketones
San Martin,De Marigorta,Dominguez
, p. 2255 - 2264 (2007/10/02)
Enaminones has been prepared and submitted to conjugate reduction with LAH and the system Al2O3/R2NH to give β-aminoketones. The latter tandem amination system has also been applied in the Mannich reaction, improving the synthesis of several new diaryl β-aminoketones. Besides, the sequential use of DMFDMA and LAH-CuI on deoxybenzoins furnishes a new route for the synthesis of enones.
SYNTHESIS OF CONJUGATED ω-DIMETHYLAMINOCARBONYL COMPOUNDS CONTAINING AN AZOMETHINE FRAGMENT
Krasnaya, Zh. A.,Bogdanov, V. S.
, p. 2057 - 2065 (2007/10/02)
Methods have been studied for synthesis of conjugated ω-dimethylaminocarbonyl compounds containing an azomethine fragment.The structures were established of all products from reaction of 2-aza-3-dimethylaminoacrolein acetal with CH-acids and of DMF acetal and β-dimethylaminoacrolein aminal with primary amines.It was shown that in many cases these reactions are accompanied by cleavage of the C=N, C-N and C=C bonds.
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.
POLYMETHINE DYES WITH HYDROCARBON BRIDGES. ENAMINO KETONES IN THE CHEMISTRY OF CYANINE DYES
Slominskii, Yu. L,Radchenko, I. D.,Popov, S. V.,Tolmachev, A. I.
, p. 1854 - 1860 (2007/10/02)
In the presence of bases alicyclic enamino ketones can react both with methyl- and with β-dialkylaminovinyl-substituted quaternary salts of nitrogen heterocycles.The reaction leads to the formation of merocyanines in which part of the chromophore extends
A New Aromatic Annelation Reaction with Two Synthons, Enaminones and 3-Oxoglutarate. Studies on the β-Carbonyl Compounds Connected with β-Polyketides. VIII
Takeuchi, Naoki,Okada, Naomi,Tobinaga, Seisho
, p. 4355 - 4359 (2007/10/02)
Reactions of the enaminones 1 with dimethyl 3-oxoglutarate in the presence of KF-AcOH or AcONa-AcOH and 18-crown-6 gave the dimethyl 2-hydroxy-1,3-benzenedicarboxylates 3, providing a new aromatic annelation reaction.Keywords - enaminone; dimethyl 3-oxoglutarate; buffer catalysis; aromatic annelation; dimethyl 2-hydroxy-1,3-benzenedicarboxylate
