3704-40-3Relevant articles and documents
Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling
Liu, Chengwei,Ji, Chong-Lei,Zhou, Tongliang,Hong, Xin,Szostak, Michal
supporting information, p. 10690 - 10699 (2021/04/09)
Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.
A 2, 5 - diaryl five-membered heterocyclic aromatic preparation method
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Paragraph 0021; 0022; 0023-0026; 0039-0041, (2019/05/15)
The invention relates to a 2, 5 - diaryl five-membered heterocyclic aromatic preparation method, the method is to turn the diaryl Iodized salt compounds, five-membered heterocyclic aromatic compound, catalyst, ligand, alkali and solvent are mixed uniformly, in 100 °C -140 °C lower sealing reaction for 24 hours, the reaction solution obtained after the reaction is complete; the reaction solution are often gauge extraction, drying, concentration, column chromatography separation to obtain the 2, 5 - diaryl five-membered heterocyclic aromatic compounds. The invention belongs to a pot of reaction of the atom economy, simple operation, high yield, can realize the large-scale production, in functional organic material, biological active compounds and pharmaceutical synthesis of better industrial application prospect.
Cu-Catalyzed Aerobic Oxidative Sulfuration/Annulation Approach to Thiazoles via Multiple Csp3-H Bond Cleavage
Wang, Xiaoyang,Qiu, Xu,Wei, Jialiang,Liu, Jianzhong,Song, Song,Wang, Wen,Jiao, Ning
supporting information, p. 2632 - 2636 (2018/05/22)
A novel and practical Cu-catalyzed aerobic oxidative synthesis of thiazoles was developed. This chemistry for the first time achieved thiazole construction from simple aldehydes, amines, and element sulfur through multiple Csp3-H bond cleavage processes. Molecular oxygen was used as a green oxidant in this oxidative protocol. The substrate scope is broad with the tolerance of aliphatic amines. The mechanistic study might promote the reaction design for a new sulfuration/annulation reaction with readily available element sulfur.
One-Pot Strategy for Thiazoline Synthesis from Alkenes and Thioamides
Alom, Nur-E,Wu, Fan,Li, Wei
supporting information, p. 930 - 933 (2017/02/26)
A convenient synthesis of a privileged pharmaceutical motif, thiazoline is accomplished. This reaction utilizes simple and readily available alkene and thioamide substrates in an intermolecular fashion via a simple one-pot procedure. A wide range of functional groups is tolerated, and the thiazoline product has been further utilized for the synthesis of the corresponding β-aminothiol and thiazole from routine hydrolysis and oxidation protocols.
Substituted azole penta-heterocyclic derivatives and solvothermal one-pot synthesis method and application thereof
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Paragraph 0083; 0084; 0085, (2016/11/02)
The invention belongs to the technical field of organic synthesis and particularly discloses a series of substituted azole penta-heterocyclic derivatives and a solvothermal one-pot synthesis method thereof. By the adoption of the solvothermal one-pot synthesis method for preparing the target product, reaction time is short, a solvent is not prone to volatilization in an airtight system, recycling can be realized, production cost is effectively reduced, the advantages of energy conservation and environment friendliness are achieved, operation is easy, yield is high, and the prepared substituted azole penta-heterocyclic derivatives have good anti-microbial biological activity and excellent photophysical properties such as electron conductivity, the fluorescence property and the ultraviolet property, thereby having very high development and application value.
A trifluorinated thiazoline scaffold leading to pro-apoptotic agents targeting prohibitins
Pérez-Perarnau, Alba,Preciado, Sara,Palmeri, Claudia Mariela,Moncunill-Massaguer, Cristina,Iglesias-Serret, Daniel,González-Gironès, Diana M.,Miguel, Miriam,Karasawa, Satoki,Sakamoto, Satoshi,Cosialls, Ana M.,Rubio-Pati?o, Camila,Saura-Esteller, José,Ram?n, Rosario,Caja, Laia,Fabregat, Isabel,Pons, Gabriel,Handa, Hiroshi,Albericio, Fernando,Gil, Joan,Lavilla, Rodolfo
supporting information, p. 10150 - 10154 (2015/03/31)
A new class of small molecules, with an unprecedented trifluorothiazoline scaffold, were synthesized and their pro-apoptotic activity was evaluated. With an EC50 in the low micromolar range, these compounds proved to be potent inducers of apopt
Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
Miura, Tomoya,Funakoshi, Yuuta,Fujimoto, Yoshikazu,Nakahashi, Junki,Murakami, Masahiro
supporting information, p. 2454 - 2457 (2015/05/27)
A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group. (Chemical Equation Presented).
Programmed synthesis of arylthiazoles through sequential C-H couplings
Tani, Satoshi,Uehara, Takahiro N.,Yamaguchi, Junichiro,Itami, Kenichiro
, p. 123 - 135 (2014/01/06)
A programmed synthesis of privileged arylthiazoles via sequential C-H couplings catalyzed by palladium or nickel catalysts has been accomplished. This versatile protocol can supply all possible arylthiazole substitution patterns (2-aryl, 4-aryl, 5-aryl, 2
Pd nanoparticle-silica nanotubes (Pd@SNTs) as an efficient catalyst for Suzuki-Miyaura coupling and sp2 C-H arylation in water
Park, Ginam,Lee, Sanghee,Son, Sang Jun,Shin, Seunghoon
supporting information, p. 3468 - 3473 (2013/12/04)
Silica nanotubes (SNTs) functionalized with Pd-NPs on the inner surface performed as efficient nano-reactors for C-C coupling in water; the nano-confinement offers minimized leaching of Pd and yet efficient mass transfer for Suzuki-Miyaura coupling and C-H arylation of thiazoles in water with very high TON.
Reigoselective arylation of thiazole derivatives at 5-position via Pd catalysis under ligand-free conditions
Liu, Xiang-Wei,Shi, Jiang-Ling,Yan, Jia-Xuan,Wei, Jiang-Bo,Peng, Kun,Dai, Le,Li, Chen-Guang,Wang, Bi-Qin,Shi, Zhang-Jie
supporting information, p. 5774 - 5777 (2013/12/04)
An efficient regioselective arylation of thiazole derivatives via Pd-catalyzed C-H activation is reported. The transformation was hypothesized through a Pd(0/II) catalytic cycle in the absence of special ligand sets. This method provided an efficient proc
