100361-20-4Relevant academic research and scientific papers
Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime
Wang, Zheng-Hai,Wang, Dong-Hui
supporting information, p. 782 - 785 (2022/01/20)
A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A catalytic mechanism, which includes Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation, is proposed.
Iron(0)-Catalyzed Transfer Hydrogenative Condensation of Nitroarenes with Alcohols: A Straightforward Approach to Benzoxazoles, Benzothiazoles, and Benzimidazoles
Putta, Ramachandra Reddy,Chun, Simin,Choi, Seung Hyun,Lee, Seok Beom,Oh, Dong-Chan,Hong, Suckchang
, p. 15396 - 15405 (2020/12/02)
The iron-catalyzed hydrogen transfer strategy has been applied to the redox condensation of o-hydroxynitrobenzene with alcohol, leading to the formation of benzoxazole derivatives. A wide range of 2-substituted benzoxazoles were synthesized in good to excellent yields without the addition of an external redox agent. A series of control experiments provided a plausible mechanism. Furthermore, the reaction system was successfully extended to the synthesis of benzothiazoles and benzimidazoles.
Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions
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Paragraph 0062; 0098, (2019/01/21)
The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.
Synthesis, protease inhibition, and antileishmanial activity of new benzoxazoles derived from acetophenone or benzophenone and synthetic precursors
Folquitto, Laís R. S.,Nogueira, Priscila F.,Espuri, Patrícia F.,Gontijo, Vanessa S.,de Souza, Thiago B.,Marques, Marcos J.,Carvalho, Diogo T.,Júdice, Wagner A. S.,Dias, Danielle F.
, p. 1149 - 1159 (2017/05/04)
Abstract: This work reports the synthesis, protease inhibition, and antileishmanial activity of ten benzoxazole derivatives, which were obtained in a three-step synthetic route from 4-hydroxy-acetophenone and 4-hydroxy-benzophenone. These benzoxazoles, the synthetic intermediates, and the starting ketones were evaluated for their inhibitory effect on the activity of cysteine (papain, rCPB2.8, and rCPB3.0) and serine (trypsin) proteases. All compounds showed significant values of IC50 against these enzymes (in the range of 0.0086–0.7612 μM for papain and 0.0075–0.5032 μM for trypsin), being more active than the standard inhibitors (1.7821 and 7.2318 μM, for E64 and TLCK, respectively). Following, all compounds were evaluated in vitro for their leishmanicidal activity against promastigote form of Leishmania amazonensis. The most active compounds were further evaluated against amastigote form and for its toxicity against murine macrophages. The benzoxazole 4d, a benzophenone derivative, and the intermediate 4-hydroxy-3-nitroacetophenone 2b showed significant antileishmanial activity (IC50 = 90.3 μM and IC50 = 130.9 μM, respectively) with selectivity indexes (5.22 and 18.09, respectively) compared to or better than those of two established leishmanicidal drugs, pentamidine (0.58) and amphotericin B (5.31). Graphical Abstract: [InlineMediaObject not available: see fulltext.].
Palladium-catalyzed direct arylation of benzoxazoles with unactivated simple arenes
Wu, Ge,Zhou, Jun,Zhang, Min,Hu, Peng,Su, Weiping
supporting information, p. 8964 - 8966 (2012/11/14)
Using CuBr2 as an additive, the Pd-catalyzed intermolecular C-H-C-H cross-coupling between benzoxazoles and unactivated simple arenes has been developed. This protocol provides a straightforward approach for the biological activity of 2-arylbenzoxazole derivatives.
