28458-93-7Relevant academic research and scientific papers
Catalytic Direct Cyanomethylenation of C(sp3)–H Bonds via a One-Step Double C–C Bond Formation
Bhadra, Sukalyan,Kumar, Jogendra,Singh, Anupam Kumar
supporting information, p. 1512 - 1517 (2022/01/27)
An elegant and catalytic procedure for the one-step cyanomethylenation of C(sp3)–H bonds adjacent to benzazoles and ketones is described herein using DMF as a C-1 unit and TMSCN as the cyanide source. The copper-mediated reaction between DMF an
Visible-Light-Induced Aerobic Oxidative Csp3?H Functionalization of Glycine Derivatives for 2-Substituted Benzoxazoles
Zhu, Zhi-Qiang,Liu, Shan,Hu, Zhi-Yu,Xie, Zong-Bo,Tang, Juan,Le, Zhang-Gao
supporting information, p. 2568 - 2572 (2021/03/31)
We report a simple oxidative Csp3?H functionalization reaction of glycine derivatives by visible-light photoredox catalysis. A wide range of glycine derivatives readily undergo the oxidative cyclization to afford various 2-substituted benzoxazoles. Importantly, this photocatalytic intramolecular dehydrogenative coupling reaction allows for the C?H functionalization of glycine derivatives involving short peptides under mild conditions, which may have value in preparing peptide-derived pharmacologically active molecules. (Figure presented.).
Copper-catalyzed oxidative cyclization of glycine derivatives toward 2-substituted benzoxazoles
Liu, Shan,Zhu, Zhi-Qiang,Hu, Zhi-Yu,Tang, Juan,Yuan, En
supporting information, p. 1616 - 1619 (2021/03/01)
A novel and straightforward intramolecular cyclization of glycine derivatives to 2-substituted benzoxazoles through copper-catalyzed oxidative C-H/O-H cross-coupling was described. A variety of glycine derivatives involving short peptides underwent cross-dehydrogenative-coupling readily to afford diverse 2-substituted benzoxazoles. The synthetic method has the advantages of simple operation, broad substrate scope and mild reaction conditions, thus providing an alternative effective approach for benzoxazole construction.
Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazolesviaredox condensation ofo-nitrophenols with acetophenones and methylquinolines
Ngo, Quoc Anh,Nguyen, Le Anh,Nguyen, Thanh Binh,Nguyen, Thi Thu Tram
supporting information, p. 6015 - 6020 (2021/07/21)
An Fe/S catalyst generatedin situfrom FeCl2·4H2O and elemental sulfur S8in the presence of a tertiary amine as a base was found to catalyze efficiently a 6e?redox condensation ofo-nitrophenols with acetophenones and methylquinolines. The condensed products 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles were obtained in reasonable yields with water as the only byproduct at a temperature as low as 80 °C.
Synthesis method of 2-aryl formyl benzoxazole compound
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Paragraph 0046-0052, (2021/06/21)
The invention discloses a synthesis method of a 2-aryl formyl benzoxazole compound, which comprises the following steps: in an oxygen-containing atmosphere and an ultrasonic environment, carrying out intramolecular cyclization-oxidation cascade reaction on N-(2-hydroxyphenyl)-2-aryl acetamide under the synergistic catalysis action of an acidic eutectic solvent and a cuprous salt, thereby obtaining the 2-aryl formyl benzoxazole compound. The method is mild in reaction condition, simple in step, green, energy-saving, high in reaction selectivity and product yield and excellent in substrate functional group compatibility, the acidic eutectic solvent/cuprous salt catalytic system can be recycled for multiple times, and the production cost is greatly reduced.
Break-and-Build Strategy for the Synthesis of 2-Benzoylbenzoxazoles from o-Aminophenols and Acetophenones
Nguyen, Le Anh,Ngo, Quoc Anh,Retailleau, Pascal,Nguyen, Thanh Binh
, p. 2098 - 2103 (2021/03/15)
Although compounds with a 2-benzoylbenzoxazole motif are biologically relevant, there are only a few methods for synthesizing them, most of which relied on multistep process or required substrates bearing activating groups. Herein, we report an efficient method for the synthesis of such compounds by direct reactions of o-aminophenols with acetophenones promoted by sulfur in DMSO. The reaction was found to proceed via a Willgerodt rearrangement-type benzoxazolation of acetophenones followed by a benzylic oxidation to reinstall the carbonyl function. This method has a broad substrate scope and good tolerance for sensitive functional groups. (Figure presented.).
Electrochemical Oxidative Functionalization of Arylalkynes: Access to α,α-Dibromo Aryl Ketones
Wang, Dan,Wan, Zhaohua,Zhang, Heng,Lei, Aiwen
, p. 1022 - 1027 (2020/12/31)
A general and effective protocol to synthesize α,α-dibromo aryl ketones has been developed via an electrochemical oxidative method. The reaction proceeds smoothly at room temperature in an undivided cell without the addition of external oxidants. In the reaction process, LiBr acts as both bromine source and supporting electrolyte. This electrooxidation strategy has good substrate applicability and functional group compatibility. Moreover, the reaction could be scaled up efficiently in a continuous flow cell. The target product could undergo further functionalization for the synthesis of some useful heterocyclic compounds. (Figure presented.).
Photoinduced remote heteroaryl migration accompanied by cyanoalkylacylation in continuous flow
Duan, Xiu,Guo, Kai,Liu, Jie,Ma, Can-Liang,Qin, Long-Zhou,Qiu, Jiang-Kai,Sun, Qi,Wu, Meng-Yu,Yuan, Xin,Zhang, Xin-Peng,Zhu, Shan-Shan
supporting information, p. 8916 - 8921 (2021/11/27)
A photoinduced 1,4-heteroaryl migration from a carbon center to a nitrogen center accompanied by a cyanoalkylacylation of heterocyclic-substituted azidyl homoallylic alcohols and cycloketone oxime esters has been described. This simple and powerful protoc
Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2H-imidazol -4-yl)amino)-phenols from 2-((5H-1,2,3-Dithiazol -5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups
Baranovsky, Ilia V.,Konstantinova, Lidia S.,Tolmachev, Mikhail A.,Popov, Vadim V.,Lyssenko, Konstantin A.,Rakitin, Oleg A.
, (2020/09/04)
A new synthetic pathway to four substituted imidazoles from readily available 2-((4-aryl (thienyl)-5H-1,2,3-dithiazol-5-ylidene)amino)phenols has been developed. Benzo[d]oxazol-2-yl(aryl (thienyl))methanimines were proved as key intermediates in their synthesis. The formation of an imidazole ring from two methanimine derivatives likely includes the opening of one benzoxazole ring followed by ring closure by intermolecular nucleophilic attack of the N-methanimine atom to a carbon atom of another methanimine.
Iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes
Tian, Tian,Wang, Xin,Lv, Leiyang,Li, Zhiping
, p. 14637 - 14640 (2020/12/02)
Herein, an iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes via distal group ipso-migration is reported. This strategy overcame the energy barrier and reversibility in the difunctionalization of unactivated alkenes with nuc
