61560-94-9Relevant academic research and scientific papers
Synthesis of α-Keto Acids via Oxidation of Alkenes Catalyzed by a Bifunctional Iron Nanocomposite
Song, Tao,Ma, Zhiming,Wang, Xiaoxue,Yang, Yong
supporting information, p. 5917 - 5921 (2021/07/31)
An efficient methodology for synthesis of α-keto acids via oxidation of alkenes using TBHP as oxidant catalyzed by a bifunctional iron nanocomposite has been established. A variety of alkenes with different functional groups were smoothly oxidized into their corresponding α-keto acids in up to 80% yield. Moreover, the bifunctional iron nanocomposite catalyst showed outstanding catalytic stability for successive recycles without appreciable loss of activity.
Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives
Ece, Hamdiye,Tange, Yuji,Yurino, Taiga,Ohkuma, Takeshi
, p. 935 - 939 (2021/02/22)
3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.
Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives
Sun, Bin,Shi, Rongcheng,Zhang, Kesheng,Tang, Xiaoli,Shi, Xiayue,Xu, Jiayun,Yang, Jin,Jin, Can
supporting information, p. 6050 - 6053 (2021/06/21)
A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.
Hypervalent Iodine(III)-Promoted Radical Oxidative C-H Annulation of Arylamines with α-Keto Acids
Long, Lipeng,Wang, Jieyan,Gu, Liuqing,Yang, Shiguang,Qiao, Liang,Luo, Guotian,Chen, Zhengwang
supporting information, p. 12084 - 12092 (2021/08/24)
A novel catalyst-free radical oxidative C-H annulation reaction of arylamines with α-keto acids toward benzoxazin-2-ones synthesis under mild conditions was developed. This hypervalent iodine(III)-promoted process eliminated the use of a metal catalyst or additive with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a radical initiator for this reaction. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A.
Visible-Light-Promoted Switchable Synthesis of C-3-Functionalized Quinoxalin-2(1H)-ones
Aganda, Kim Christopher C.,Hong, Boseok,Lee, Anna
supporting information, p. 1443 - 1448 (2021/01/26)
A visible-light-promoted synthesis of quinoxalin-2(1H)-ones has been developed using 9-mesityl-10-methylacridinium perchlorate as an organo-photocatalyst. The atmosphere-controlled method (Ar/air) enabled the selective synthesis of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones under mild reaction conditions without the use of any metal catalysts or toxic reagents. A fluorescent labelling experiment showed that hydroxyl-containing quinoxalin-2(1H)-ones may have utility in various biological applications as potent fluorophores. (Figure presented.).
Direct 1,2-Dicarbonylation of Alkenes towards 1,4-Diketones via Photocatalysis
Chen, Bin,Cheng, Yuan-Yuan,Hou, Hong-Yu,Lei, Tao,Tung, Chen-Ho,Wu, Li-Zhu,Yu, Ji-Xin
supporting information, p. 26822 - 26828 (2021/11/17)
1,4-Dicarbonyl compounds are intriguing motifs and versatile precursors in numerous pharmaceutical molecules and bioactive natural compounds. Direct incorporation of two carbonyl groups into a double bond at both ends is straightforward, but also challenging. Represented herein is the first example of 1,2-dicarbonylation of alkenes by photocatalysis. Key to success is that N(n-Bu)4+ not only associates with the alkyl anion to avoid protonation, but also activates the α-keto acid to undergo electrophilic addition. The α-keto acid is employed both for acyl generation and electrophilic addition. By tuning the reductive and electrophilic ability of the acyl precursor, unsymmetric 1,4-dicarbonylation is achieved for the first time. This metal-free, redox-neutral and regioselective 1,2-dicarbonylation of alkenes is executed by a photocatalyst for versatile substrates under extremely mild conditions and shows great potential in biomolecular and drug molecular derivatization.
Diazotrifluoroethyl Radical: A CF3-Containing Building Block in [3 + 2] Cycloaddition
Zhao, Wen-Wen,Shao, Yong-Chao,Wang, An-Ni,Huang, Jia-Li,He, Chun-Yang,Cui, Bao-Dong,Wan, Nan-Wei,Chen, Yong-Zheng,Han, Wen-Yong
supporting information, p. 9256 - 9261 (2021/12/06)
We present herein a visible-light-induced [3 + 2] cycloaddition of a hypervalent iodine(III) reagent with α-ketoacids for the construction of 5-CF3-1,3,4-oxadiazoles that are of importance in medicinal chemistry. The reaction proceeds smoothly without a photocatalyst, metal, or additive under mild conditions. Different from the well-established trifluorodiazoethane (CF3CHN2), the diazotrifluoroethyl radical [CF3C(·)N2], a trifluoroethylcarbyne (CF3C?:) equivalent and an unusual CF3-containing building block, is involved in the present reaction system.
Arylglyoxylic acid as well as preparation method and application thereof
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Paragraph 0053-0057, (2021/01/15)
The invention relates to arylglyoxylic acid as well as a preparation method and application thereof, and the method comprises the following steps: carrying out hydrolysis reaction on arylglyoxylonitrile oxime as shown in a formula (I) under the catalysis of an inorganic acid to obtain arylglyoxylic acid as shown in a formula (II). The arylglyoxylic acid prepared by the preparation method is high in yield, high in product purity, simple to operate, environment-friendly and pollution-free. The arylglyoxylic acid is used as a fine chemical synthesis intermediate.
General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling
Li, Bowen,Aliyu, Muinat A.,Gao, Zhenhua,Li, Tiejun,Dong, Wei,Li, Junchen,Shi, Enxue,Tang, Wenjun
, p. 4974 - 4978 (2020/07/03)
A general synthesis of chiral α,α-diaryl carboxamides is developed by enantioselective cross-coupling between 2-bromo-2-aryl carboxamides and arylboronic acids, leading to a series of chiral α,α-diaryl carboxamides with various electronic properties and functionalities in moderate to excellent enantioselectivities and yields. The employment of a sterically bulky chiral P,P═O ligand L2 is critical for the reactivity and selectivity. This protocol is applied to an efficient asymmetric synthesis of a key intermediate of dopamine receptor agonist SKF 38393.
Metal-free C3-H acylation of quinoxalin-2(1: H)-ones with α-oxo-carboxylic acids
Li, Yu,Ni, Hangcheng,Shi, Xingzi,Zhang, Xiaoning,Zhao, Fei,Zhao, Jingwei
supporting information, p. 6558 - 6563 (2020/09/04)
Direct C3-H acylation of quinoxalin-2(1H)-ones with α-oxocarboxylic acids under thermo conditions promoted by PIDA has been achieved in a moderate to good yield in a very fast manner. Mechanistic study revealed that the reaction proceeds via a radical pro
