442900-08-5Relevant academic research and scientific papers
Zinc Hydroxide-Catalyzed Asymmetric Allylation of Acetophenones with Amido-Functionalized Allylboronate in Water
Sengoku, Tetsuya,Maegawa, Ryunosuke,Imamura, Hiroki,Wada, Mitsuo,Yoda, Hidemi
supporting information, p. 2397 - 2418 (2020/04/29)
Enantioselective allylation of aldehydes and ketones is a widely used approach for preparing chiral homoallylic alcohols, however, most of the reactions are still mainly performed in organic solvents. Considering their environmental impact, expansion of synthetic technology in water has the highest priority in the organic chemistry field. Here, we report enantioselective reaction of water-stable amido-functionalized allylboronates with acetophenone derivatives in water. The reaction was catalyzed with zinc hydroxide and a didecylamino-functionalized chiral aminophenol reagent, affording a variety of homoallylic alcohols in up to 99% yield. There is a definite proportional correlation between the enantioselectivity and the size of an ortho-substituent on the substrate, and the enantiomeric excess of the product reached up to 98%. (Figure presented.).
Systematic Study of the Glutathione Reactivity of N-Phenylacrylamides: 2. Effects of Acrylamide Substitution
Birkholz, Adam,Kopecky, David J.,Volak, Laurie P.,Bartberger, Michael D.,Chen, Yuping,Tegley, Christopher M.,Arvedson, Tara,McCarter, John D.,Fotsch, Christopher,Cee, Victor J.
, p. 11602 - 11614 (2020/12/04)
A comprehensive understanding of structure-reactivity relationships is critical to the design and optimization of cysteine-targeted covalent inhibitors. Herein, we report glutathione (GSH) reaction rates for N-phenyl acrylamides with varied substitutions at the α- and β-positions of the acrylamide moiety. We find that the GSH reaction rates can generally be understood in terms of the electron donating or withdrawing ability of the substituent. When installed at the β-position, aminomethyl substituents with amine pKa's > 7 accelerate, while those with pKa's 7 slow the rate of GSH addition at pH 7.4, relative to a hydrogen substituent. Although a computational model was able to only approximately capture experimental reactivity trends, our calculations do not support a frequently invoked mechanism of concerted amine/thiol proton transfer and C-S bond formation and instead suggest that protonated aminomethyl functions as an electron-withdrawing group to reduce the barrier for thiolate addition to the acrylamide.
Electrophilic Amide Allylation of 3-Heterosubstituted Oxindoles: A Route to Spirocyclic 2-Oxindoles Containing the α-Methylene-γ-butyrolactam Structure
Sengoku, Tetsuya,Hayashi, Daichi,Takahashi, Masaki,Yoda, Hidemi
, p. 1813 - 1820 (2018/04/27)
This article reports a new route to access spirocyclic 2-oxindoles containing the α-methylene-γ-butyrolactam structure via “electrophilic amide allylation”. The key reaction was accomplished by using acetoxy methacrylamides and tetrakis(triphenylphosphine)palladium as catalyst, affording a variety of the amide allylated products in excellent yields. The successful cyclization of these products has demonstrated the potential utility of this approach to offer a practical synthesis of spirocyclic oxindoles.
XANTHENE DERIVATIVE, PRODUCTION METHOD THEREOF, AND METHOD OF DETECTING CANCER CELLS USING THE DERIVATIVE
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Paragraph 0141, (2018/04/14)
PROBLEM TO BE SOLVED: To provide a fluorescent probe for detecting cancer cells in the co-presence of normal cells. SOLUTION: There is provided a xanthene derivative represented by general formula (1). SELECTED DRAWING: Figure 4 COPYRIGHT: (C)2018,JPOandINPIT
UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions
Zheng, Lewei,Huang, Hongli,Yang, Chao,Xia, Wujiong
supporting information, p. 1034 - 1037 (2015/03/30)
UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.
Oxidant-Free Rhodium(I)-Catalyzed Difunctionalization of Acrylamide: An Efficient Approach to Synthesize Oxindoles
Li, Chen-Chen,Yang, Shang-Dong
supporting information, p. 2142 - 2145 (2015/05/13)
(Figure Presented) The first rhodium(I)-catalyzed difunctionalization of arylacrylamides to synthesize oxindoles is developed, and it does not require the assistance of an oxidant. This method provides an efficient approach to generate various useful functionalized oxindoles, some of which cannot be easily accessed by previous approaches.
Iron-catalyzed aerobic difunctionalization of alkenes: A highly efficient approach to construct oxindoles by C-S and C-C bond formation
Shen, Tao,Yuan, Yizhi,Song, Song,Jiao, Ning
supporting information, p. 4115 - 4118 (2014/04/03)
A novel iron-catalyzed efficient approach to construct sulfone-containing oxindoles, which play important roles in the structural library design and drug discovery, has been developed. The use of readily available benzenesulfinic acids, an inexpensive iron salt as the catalyst, and air as the oxidant makes this sulfur incorporation protocol very efficient and practical. This journal is the Partner Organisations 2014.
