35040-28-9Relevant academic research and scientific papers
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.
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.).
CuI-catalyzed and air promoted oxidative cyclization for one-pot synthesis of polyarylated oxazoles
Hu, Ping,Wang, Qiang,Yan, Yizhe,Zhang, Shuai,Zhang, Baiqun,Wang, Zhiyong
, p. 4304 - 4307 (2013/08/23)
A facile CuI-catalyzed and air promoted oxidative cyclization was developed for the synthesis of polyarylated oxazoles. By virtue of this method, a variety of arylated oxazoles could be easily synthesized from readily available starting materials at room temperature in air. The Royal Society of Chemistry 2013.
Synthesis of 2-substituted 4,5-diphenyloxazoles under solvent-free microwave irradiation conditions
Lee, Jong Chan,Seo, Jang-Woo,Baek, Jong Wook
, p. 2159 - 2162 (2008/02/07)
A novel method for the direct conversion of deoxybenzoin into 2-alkyl-4,5-diphenyloxazoles and 2-aryl-4,5-diphenyloxazoles has been developed using treatment of HTIB and nitriles under solvent-free microwave irradiation conditions. Copyright Taylor & Fran
