39659-76-2Relevant academic research and scientific papers
Highly Chemoselective Solvent-Free Synthesis of 1,3,5-Triaryl-1,5-diketones: Crystallographic Investigation and Intramolecular Weak Bifurcated H Bonds Involving Aliphatic C-H Group
Borovkov, Victor,Guo, Jianxin,Hu, Xiaoyun,Shan, Zixing,Xiong, Changkun,Yin, Zhongyou
supporting information, p. 2143 - 2147 (2019/11/25)
Several 1,3,5-triaryl-1,5-diketones have been chemoselectively synthesized under solvent-free conditions. It was found that intramolecular weak bifurcated H-bonds interaction of aliphatic C-H group plays a decisive role in the structural arrangement of 3-
In situ formed acetals facilitated direct Michael addition of unactivated ketones
Koppolu, Srinivasa Rao,Balamurugan, Rengarajan
, p. 1186 - 1192 (2017/02/10)
TfOH-promoted synthesis of 1,5-diketones by the Michael reaction of unactivated ketones with chalcones has been described. Acetals formed under HC(OMe)3/TfOH conditions generate the required enol-equivalents for a smooth Michael reaction. A wide array of symmetrical and unsymmetrical 1,5-diketones has been synthesised.
N-Heterocyclic Carbene-Catalysed Mukaiyama-Michael Reaction and Mukaiyama Aldol/Mukaiyama-Michael Three-Component Coupling Reaction
Nguyen, Kim,Lupton, David W.
, p. 436 - 441 (2017/04/07)
An N-heterocyclic carbene-catalysed Mukaiyama-Michael addition between several trimethylsilyl (TMS) enol ethers and chalcone derivatives has been discovered. In addition, a related reaction cascade involving dehydrative Mukaiyama aldol followed by a Mukaiyama-Michael addition process has been developed. The later reaction can also be achieved as a three-component coupling reaction. The enantioselective variant of these reactions has been examined with homochiral catalysts. Though these catalysts were active, they fail to achieve enantioinduction.
Lipase-Catalysed Addition of Pyrrolidine to Chalcone and Benzylidene Malonate Derivatives
Habibi,Yousefi,Kheyrabadi,Mohammadi,Moemeni,Nazari
, p. 861 - 864 (2015/12/26)
The porcine pancreas lipase (PPL) type II catalyzes the aminolysis of benzylidene malonates by regiospecific amidation of substrates and afforded the Z-isomer; no E-isomer or diamide byproducts were observed. PPL also catalyzes Michael addition of acetophenone to various derivatives of chalcones.
Copper-catalyzed synthesis of 1,3,5-triarylpentane-1,5-diones from α,β-unsaturated ketones
Li, Zheng,Wen, Gong,He, Lili,Li, Jiasheng,Jia, Xianggui,Yang, Jingya
, p. 52121 - 52125 (2015/06/25)
An efficient method for copper catalyzed synthesis of 1,3,5-triarylpentane-1,5-diones using α,β-unsaturated ketones as unique starting materials is described. The protocol offers several advantages such as simple, inexpensive reagents, mild reaction condi
A facile one-pot synthesis of 2,4,6-triarylpyridine in DMSO
Min, Zhen-Li,Yin, Ting-Zi,Hu, Xia-Min
, p. 7977 - 7980 (2015/02/02)
A facile, efficient and practical method for the one-pot synthesis of 2,4,6-triarylpyridines starting from acetophenones, aryl aldehydes and ammonium acetate by the use of catalytic amounts of 40 % potassium hydroxide in dimethyl sulfoxide is presented. T
Unexpected synthesis of 1,3,5-triarly-1,5-diketones from aryl ketones via di-enamine mechanism
Ge, Zemei,Li, Runtao,Liu, Bin,Pang, Yi,Wang, Junfeng
, p. 9240 - 9244 (2020/12/05)
An unexpected reaction of aryl ketone with acetohydrazone of aromatic aldehyde via 1,2-di-enamine/di-iminium mechanism was discovered, leading to efficient synthesis of 1,3,5-triaryl-1,5-diketones in good to excellent yields.
Microwave-assisted, tetrabutylammonium hydroxide catalysed 1,4-addition of water to α,β-unsaturated ketones and α,β-ynones in aqueous solution
Lee, Hyejeong,Jun, Chul-Ho
, p. 48331 - 48335 (2014/12/11)
Microwave-assisted, tetrabutylammonium hydroxide catalysed 1,4-addition reactions of water to α,β-unsaturated ketones and α,β-ynones take place efficiently in water. Reactions of the resulting β-hydroxy ketones lead to the formation of either C-C bond cleavage or annulation products. This journal is
Facile microwave-assisted michael addition of diphenacyl sulfides to chalcones under solvent-free conditions: Generation of symmetrical and unsymmetrical 1,5-diketones
Paul, Nidhin,Shanmugam, Muniyappapillai Jeganathan,Muthusubramanian, Shanmugam
, p. 129 - 138 (2012/11/07)
The article describes an efficient and environmentally friendly Michael addition of 2-[(2-oxo-2-phenylethyl)sulfanyl]-1-phenyl-1-ethanones (diphenacyl sulfides) to substituted chalcones using microwave irradiation under solvent-free conditions, affording
An easy access to bioactive 13-hydroxylated and 11,13-dihydroxylated sesquiterpene lactones (SLs) through Michael addition of a nucleophilic hydroxyl group
Macías, Francisco A.,García-Díaz, María D.,Massanet, Guillermo M.,Gómez-Madero, José F.,Fronczek, Frank R.,Galindo, Juan C.G.
experimental part, p. 10996 - 11006 (2009/04/11)
The addition of a hydroxyl group to α,β-unsaturated carbonyl systems provides a new and easy access to bioactive difunctionalized sesquiterpene lactones (SLs) through a Michael addition to the α-methylene-γ-lactone system. The use of HMPA to enhance the nucleophilic properties of the hydroxyl groups and to stabilize the enolate is discussed. Also, we present a proposal for the mechanism based on the experimental data obtained. The scope and usefulness of the reaction are explored with other substrates and is limited by the need for a certain level of steric hindrance to avoid chain polycondensations. Nevertheless, the reaction works with esters, ketones and aldehydes. The absolute stereochemistry of some products has been elucidated by X-ray diffraction analysis. The synthesis of a natural SL using this methodology and the correction of the structure of another illustrate the usefulness of this reaction.
