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-
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.
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.
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
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.
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
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
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.
