573-34-2Relevant articles and documents
Palladium-catalyzed C-H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles
Dai, Ling,Yu, Shuling,Shao, Yinlin,Li, Renhao,Chen, Zhongyan,Lv, Ningning,Chen, Jiuxi
supporting information, p. 1376 - 1379 (2021/02/22)
An efficient and straightforward protocol for the assembly of the pharmaceutically and biologically valuable oxazole skeleton is achieved for the first time from readily available simple arenes and functionalized aliphatic nitriles. This transformation in
Sonochemical synthesis of polyarylated oxazoles as potential cytotoxic agents
Kandula, Venkata Ramana,Pothireddy, Mohanreddy,Babu, K. Suresh,Kapavarapu, Ravikumar,Dandela, Rambabu,Pal, Manojit
supporting information, (2021/04/02)
The ultrasound assisted facile, rapid and one-pot synthesis of 2-aryl substituted 4,5-diphenyloxazoles was achieved via the reaction of commercially available benzoin (or 2-hydroxy-2-phenylacetophenone) with benzylamines in the presence of IBX under mild conditions. The methodology involved initial IBX mediated conversion of benzoin to benzil and then reaction with benzylamine followed by intramolecular cyclization (C[sbnd]O bond formation) and finally aromatization in the presence of air in the same pot. The methodology afforded a variety of desired products that were assessed for their cytotoxic properties against a number of cancerous and a non-cancerous cell lines. Compounds 3h, 3n and 3o showed promising growth inhibition of these cell lines except the non-cancerous one and interactions with SIRT1 in silico as well as in vitro.
Iron-Catalyzed Cycloaddition of Amides and 2,3-Diaryl-2 H-azirines to Access Oxazoles via C-N Bond Cleavage
Zhao, Mi-Na,Ning, Gui-Wan,Yang, De-Suo,Fan, Ming-Jin,Zhang, Sheng,Gao, Peng,Zhao, Li-Fang
, p. 2957 - 2964 (2021/02/01)
A novel and efficient iron-catalyzed cycloaddition reaction using readily available 2,3-diaryl-2H-azirines and primary amides is reported. A wide range of trisubstituted oxazoles could be achieved in good yields with good functional group compatibility. In this transformation, two C-N bonds were cleaed and new C-N and C-O bonds were formed.
Synthesis method of 2, 4, 5-trisubstituted oxazole compound
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Paragraph 0036-0044; 0076-0078, (2021/06/23)
The invention discloses a simple and efficient synthesis method of a 2, 4, 5-trisubstituted oxazole compound, which comprises the following steps: adding a cyano-substituted ester compound, simple aromatic hydrocarbon, palladium acetylacetonate and dimeth
Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions
Song, A-Xiang,Zeng, Xiao-Xiao,Ma, Bei-Bei,Xu, Chang,Liu, Feng-Shou
, p. 3524 - 3534 (2020/10/09)
With the aim of developing a facile and efficient method to access structurally intriguing and valuable functionalized (hetero)aryls, two unsymmetrical Pd-PEPPSI-type NHC complexes (PEPPSI, pyridine-enhanced precatalyst preparation, stabilization, and initiation; NHC, N-heterocyclic carbene) were designed and synthesized to catalyze the direct arylation of heteroarenes with (hetero)aryl bromides. The results demonstrated that the utilization of this "unsymmetrical"strategy led to much higher efficiency in comparison to the commonly used C2-symmetric Pd-PEPPSI-type NHC complexes. Furthermore, a broad range of heteroaromatics and (hetero)aryl bromide partners with a wide variety of functional groups were all amenable to the developed protocol even at as low as 0.05 mol % catalyst loading and under aerobic conditions. More importantly, along with our study, we also found that the present protocol could provide expedient access to the gram-scale synthesis of the muscle relaxant drug dantrolene and conjugated mesopolymers.
Divergent Palladium-Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins
Chen, Jiuxi,Chen, Zhongyan,Dai, Ling,Shao, Yinlin,Xiong, Wenzhang,Xu, Tong,Yu, Shuling
supporting information, (2020/04/15)
A palladium-catalyzed tandem reaction of cyanomethyl benzoates with arylboronic acids has been achieved. Substitution at the 2-position of cyanomethyl benzoates was found to be crucial for the selective synthesis of oxazoles and isocoumarins. Cyanomethyl
Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature
Charpe, Vaibhav Pramod,Hwang, Kuo Chu,Sagadevan, Arunachalam
, p. 4426 - 4432 (2020/08/10)
We have developed the visible light induced simple copper(ii) chloride catalyzed oxidation of diarylacetylenes to α-diketones by molecular oxygen at room temperature. The in situ generated copper(ii)-superoxo complex is a light-absorbing species that oxidizes inert diarylacetylenes to α-diketones. In contrast to reported photochemical processes, the current oxidation protocol does not require any exogenous photocatalyst or radical initiator. The green chemistry metrics evaluation signifies that the E-factor for the current oxidation process is ~2.3 times better than that of reported photochemical processes. The current reaction scores 63 on the EcoScale of 0-100, indicating an adequate synthesis process. Thus, the overall oxidation process is simple, environmentally benign, and economically feasible. This journal is
Lewis acid-mediated defluorinative [3+2] cycloaddition/aromatization cascade of 2,2-difluoroethanol systems with nitriles
Hsieh, Min-Tsang,Lee, Kuo-Hsiung,Kuo, Sheng-Chu,Lin, Hui-Chang
, p. 1605 - 1610 (2018/03/05)
The properties of C?F bonds, including high thermal and chemical stability, make derivatization of organic fluorine-containing compounds by the activation of the C?F bond and subsequent functionalization quite challenging. We herein report a Lewis acid-mediated defluorinative cycloaddition/aromatization cascade of 2,2-difluoroethanols with nitriles as a novel synthetic method for the preparation of 2,4,5-trisubstituted oxazoles. This reaction, which involves cleavage of two C?F bonds and the consecutive formation of C?O and C?N bonds in a one-pot fashion, features a broad substrate scope and moderate to high reaction yields. Mechanistic studies revealed that the reaction is initiated by the Lewis acid-mediated ring closure of the 2,2-difluoroethanol to produce the fluoroepoxide intermediate. (Figure presented.).
Ionization and Anion-π+ Interaction: A New Strategy for Structural Design of Aggregation-Induced Emission Luminogens
Wang, Jianguo,Gu, Xinggui,Zhang, Pengfei,Huang, Xiaobo,Zheng, Xiaoyan,Chen, Ming,Feng, Haitao,Kwok, Ryan T. K.,Lam, Jacky W. Y.,Tang, Ben Zhong
supporting information, p. 16974 - 16979 (2017/11/30)
Recent years have witnessed the significant role of anion-π+ interactions in many areas, which potentially brings the opportunity for the development of aggregation-induced emission (AIE) systems. Here, a new strategy that utilized anion-π
A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C-H Amination and Alkoxylation
Yamamoto, Chiaki,Takamatsu, Kazutaka,Hirano, Koji,Miura, Masahiro
supporting information, p. 9112 - 9118 (2017/09/11)
A directing-group-controlled, copper-catalyzed divergent approach to indoles and oxazoles from enamides has been developed. The picolinamide-derived enamides undergo the intramolecular aromatic C-H amination in the presence of a Cu(OPiv)2 catalyst and an MnO2 oxidant to form the corresponding indoles in good yields. On the other hand, simpler aryl- or alkyl-substituted enamides are converted to the 2,4,5-trisubstituted oxazole frameworks via vinylic C-H alkoxylation under identical conditions. The copper catalysis can provide uniquely divergent access to indole and oxazole heteroaromatic cores of great importance in medicinal and material chemistry.