28467-36-9Relevant articles and documents
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.
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.
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.
