58929-06-9Relevant academic research and scientific papers
Effects of substituents in the β-position of 1,3-dicarbonyl compounds in bromodimethylsulfonium bromide-catalyzed multicomponent reactions: A facile access to functionalized piperidines
Khan, Abu T.,Parvin, Tasneem,Choudhury, Lokman H.
, p. 8398 - 8402 (2008)
(Chemical Equation Presented) 1,3-Dicarbonyl compounds can be converted to Mannich-type products A or highly functionalized piperidines B in the presence of a catalytic amount of bromodimethylsulfonium bromide (BDMS). The combination of aromatic aldehyde, amine, and 1,3-dicarbonyl compounds in the presence of a catalytic amount of BDMS leads to the formation of Mannich-type product A when R is a non-enolizable carbon or an alkoxy group, whereas in cases when R = CH3, the same combination yielded highly functionalized piperidines B. A synthetic study and mechanistic proposal are presented.
An efficient synthesis of β-amino esters via Zn(OTf) 2-catalyzed Mannich-type reaction
Shou, Wang-Ge,Yang, Yun-Yun,Wang, Yan-Guang
, p. 1845 - 1847 (2006)
A Zn(OTf)2-catalyzed Mannich-type reaction of the electron-deficient aromatic amines with the electron-deficient aromatic aldehydes and diethyl malonic ester was described. This three-component reaction afforded the corresponding β-amino esters
Cooperative catalysis with block copolymer micelles: A combinatorial approach
Bukhryakov, Konstantin V.,Desyatkin, Victor G.,O'Shea, John-Paul,Almahdali, Sarah R.,Solovyeva, Vera,Rodionov, Valentin O.
supporting information, p. 76 - 80 (2015/03/05)
A rapid approach to identifying complementary catalytic groups using combinations of functional polymers is presented. Amphiphilic polymers with "clickable" hydrophobic blocks were used to create a library of functional polymers, each bearing a single functionality. The polymers were combined in water, yielding mixed micelles. As the functional groups were colocalized in the hydrophobic microphase, they could act cooperatively, giving rise to new modes of catalysis. The multipolymer "clumps" were screened for catalytic activity, both in the presence and absence of metal ions. A number of catalyst candidates were identified across a wide range of model reaction types. One of the catalytic systems discovered was used to perform a number of preparative-scale syntheses. Our approach provides easy access to a range of enzyme-inspired cooperative catalysts.
One-pot synthesis of β-amino esters by recyclable magnetic organocatalyst-catalysed Mannich-type reaction
Huang, Yibo,Guan, Dan,Wang, Liang
, p. 297 - 299 (2014/06/09)
L-cysteine supported on an iron oxide magnetic nanoparticle was prepared by a facile and simple method. The catalyst was effectively applied to the one-pot synthesis of β-amino esters in moderate to good yield. Moreover, the magnetic organocatalyst could be readily recovered and reused up to five times without significant loss of its catalytic activity.
One-pot synthesis of mannich bases under solvent-free conditions
Demirkol, Onur,Akbaslar, Dilek,Giray, Sultan,Anil, B. Baris
supporting information, p. 1279 - 1285 (2014/04/17)
A mild and practically convenient one-pot procedure for the Mannich reaction via condensation of amines, aldehydes and malonates, β-ketoesters, or β-dicarbonyl compounds has been carried out without using any organic solvent, metallic catalyst, or Lewis acids or bases at room temperature. The present protocol offers several advantages, such as goods yields, simple procedure with easy workup, and the absence of any volatile, hazardous organic solvents and metallic catalyst.
LiClO4-accelerated three-component Mannich-type reaction of diethyl malonate with imines: An efficient synthesis of β-amino esters under solvent-free conditions
Aryanasab, Fezzeh,Saidi, Mohammad R.
body text, p. 4036 - 4044 (2009/04/06)
LiClO4 is used as catalyst for direct Mannich-type reaction of aryl aldehydes, aryl amines, and diethyl malonic ester under solvent-free conditions. This three-component reaction afforded the corresponding β-amino esters in good yields with simple and env
Bromodimethylsulfonium bromide catalyzed three-component Mannich-type reactions
Khan, Abu T.,Parvin, Tasneem,Choudhury, Lokman H.
scheme or table, p. 834 - 839 (2009/04/11)
Bromodimethylsulfonium bromide catalyzes Mannich-type reactions of a variety of aldimines, generated in situ from aldehydes and anilines, with enolizable ketones or diethyl malonate in three-component reactions to afford the corresponding β-amino carbonyl compounds. The salient features of this protocol are: shorter reaction times, simplicity of the procedure, good to excellent yields, avoidance of aqueous workup and column-chromatographic separations, and high stereoselectivities. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Synthesis of β-amino carbonyl compounds via a Zn(OTf)2-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds
Yang, Yun-Yun,Shou, Wang-Ge,Wang, Yan-Guang
, p. 10079 - 10086 (2007/10/03)
A Zn(OTf)2-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds was described. This one-pot three-component reaction afforded the corresponding β-amino carbonyl compounds, β-amino esters, and β-amino ketones in good to excellent yields. The reaction was also applied for the liquid-phase synthesis of β-amino carbonyl compound library using PEG as a support.
