41126-22-1Relevant academic research and scientific papers
Metal-Free, DBU-Mediated, Microwave-Assisted Synthesis of Benzo[c]xanthones by Tandem Reactions of Alkynyl-1,3-diketones
Liang, Yi-En,D. Barve, Balaji,Kuo, Yao-Haur,Fang, Hsu-Wei,Kuo, Ting-Shen,Li, Wen-Tai
supporting information, p. 505 - 511 (2020/12/01)
A base-mediated, green, microwave-assisted efficient preparation of a diverse benzoxanthone library from variety of readily accessible γ-alkynyl 1,3-diketones is reported. The synthesis is based on tandem reactions involving intramolecular cyclization, propargyl-allenyl isomerization, and electrocyclization in one pot. Some of the benzoxanthones are also synthesized by the one-pot reaction of 1,3-diketone and alkynyl bromide under basic heating conditions. This transformation also results in the construction of one new C?C bond and one new C?O bond. (Figure presented.).
Identification of new aryl hydrocarbon receptor (AhR) antagonists using a zebrafish model
Jeong, Jieun,Kim, Kun-Hee,Kim, Dong-Young,Chandrasekaran, Gopalakrishnan,Kim, Minhee,Pagire, Suvarna H.,Dighe, Mahesh,Choi, Eun Young,Bak, Su-Min,Kim, Eun-Young,Shin, Myung-Geun,Choi, Seok-Yong,Ahn, Jin Hee
, (2019/08/01)
A new series of 1,3-diketone, heterocyclic and α,β-unsaturated derivatives were synthesized and evaluated for their AhR antagonist activity using zebrafish and mammalian cells. Compounds 1b, 2c, 3b and 5b showed significant AhR antagonist activity in a transgenic zebrafish model. Among them, compound 3b, and 5b were found to have excellent AhR antagonist activity with IC50 of 3.36 nM and 8.3 nM in a luciferase reporter gene assay. In stem cell proliferation assay, compound 5b elicited marked HSC expansion.
An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources
Chen, Pei,Zhang, Qian-Qian,Guo, Jia,Chen, Lu-Lu,Wang, Yan-Bo,Zhang, Xiao
, p. 6958 - 6966 (2018/10/02)
An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.
Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones
He, Zhen,Qi, Xiaotian,She, Zhijie,Zhao, Yinsong,Li, Shiqing,Tang, Junbin,Gao, Ge,Lan, Yu,You, Jingsong
supporting information, p. 1403 - 1411 (2017/02/10)
A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.
Transition-metal-free formal decarboxylative coupling of ?±-oxocarboxylates with ?±-bromoketones under neutral conditions: A simple access to 1,3-diketones
He, Zhen,Qi, Xiaotian,Li, Shiqing,Zhao, Yinsong,Gao, Ge,Lan, Yu,Wu, Yiwei,Lan, Jingbo,You, Jingsong
supporting information, p. 855 - 859 (2015/02/05)
A transition-metal-free formal decarboxylative coupling reaction between ?±-oxocarboxylates and ?±-bromoketones to synthesize 1,3-diketone derivatives is presented. In this reaction, a broad scope of substrates can be employed, and neither a metal-based reagent nor an additional base is required. DFT calculations reveal that this reaction proceeds through a coupling followed by decarboxylation mechanism and the ?±-bromoketone unprecedentedly serves as a nucleophile under neutral conditions. The rate-determining step is an unusual hydrogen-bond-assisted enolate formation by thermolysis.
Asymmetric transfer hydrogenation of unsymmetrical benzils
Zhang, Hao,Feng, Dandan,Sheng, Haibo,Ma, Xuebing,Wan, Jinwei,Tang, Qian
, p. 6417 - 6423 (2014/02/14)
In this paper, the asymmetric transfer hydrogenation of unsymmetrical benzils with m, p-substituents was conducted with a substrate/catalyst molar ratio of 100 at 40°C for 24 h to produce (S,S)-hydrobenzoins in good yields (76.2% to 97.1%) with high diastereomeric (syn/anti = 10.8 to 29.7/1) and enantiomeric purities (86.1%ee syn to 98.9%ee syn). Unfortunately, the unsymmetrical benzils with the o-substituents such as electron-donating (R = CH3, OCH3) and electron-withdrawing groups (R = F, Cl, CF3) resulted in poor yields (0% to 31.2%), even at 40°C for 72 h. These products had inefficient diastereoselectivities (syn/anti = 1.5 to 5.0/1) caused by steric effects. Furthermore, the results of a dynamic-kinetic study were used to propose a plausible reaction pathway of unsymmetrical benzil using 3-methoxy-1,2-diphenyl ethanedione as an example.
GLUCOKINASE ACTIVATORS
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Page/Page column 48-49, (2010/11/28)
Compounds, pharmaceutical compositions, kits and methods are provided for use with glucokinase that comprise a compound selected from the group consisting of: wherein the variables are as defined herein.
