1258498-75-7Relevant academic research and scientific papers
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)
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.
Synthesis method of 2-aryl formyl benzoxazole compound
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Paragraph 0046-0052; 0057-0060, (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.
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.
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
supporting information, 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.).
Acid-Catalyzed Condensation of o-Phenylenediammines and o-Aminophenols with α-Oxodithioesters: A Divergent and Regio? selective Synthesis of 2-Methylthio-3-Aryl/Heteroarylquinoxalines and 2-Acylbenzoxazoles
Anil, Seegehally M,Kiran, Kuppalli R,Rangappa, Kanchugarakoppal S,Sadashiva, Maralinganadoddi P,Shruthi, Jeegundipattana B,Sukrutha, Kodipura P,Swaroop, Toreshettahally R
, p. 4205 - 4214 (2019/11/14)
o-Phenylenediammines and o-Aminophenols were reacted with α-oxodithioesters in a highly regioselective fashion to give 2-methylthio-3-Aryl/heteroarylquinoxalines and 2-Acylbenzoxazoles in 55-94percent and 45-86percent, respectively, in the presence of p-T
Palladium(II)/N-heterocyclic carbene-catalyzed direct C-H acylation of heteroarenes with N-acylsaccharins
Karthik, Shanmugam,Gandhi, Thirumanavelan
supporting information, p. 5486 - 5489 (2017/11/06)
N-Acylsaccharin represents a facile acyl group transfer agent to heteroarenes in the presence of Pd(II)/NHC complexes appended with a pyrene unit. Catalytic acylation of heteroarenes was enhanced by the noncovalent interaction between the pyrene unit and
An Electrophilic Approach to the Palladium-Catalyzed Carbonylative C-H Functionalization of Heterocycles
Tjutrins, Jevgenijs,Arndtsen, Bruce A.
supporting information, p. 12050 - 12054 (2015/10/05)
A palladium-catalyzed approach to intermolecular carbonylative C-H functionalization is described. This transformation is mediated by PtBu3-coordinated palladium catalyst and allows the derivatization of a diverse range of heterocycles, including pyrroles, indoles, imidazoles, benzoxazoles, and furans. Preliminary studies suggest that this reaction may proceed via the catalytic formation of highly electrophilic intermediates. Overall, this provides with an atom-economical and general synthetic route to generate aryl-(hetero)aryl ketones using stable reagents (aryl iodides and CO) and without the typical need to exploit pre-metalated heterocycles in carbonylative coupling chemistry.
Cobalt-Catalyzed Decarboxylative 2-Benzoylation of Oxazoles and Thiazoles with α-Oxocarboxylic Acids
Yang, Ke,Chen, Xinyong,Wang, Yuqi,Li, Wanqing,Kadi, Adnan A.,Fun, Hoong-Kun,Sun, Hao,Zhang, Yan,Li, Guigen,Lu, Hongjian
, p. 11065 - 11072 (2015/11/18)
Cobalt-catalyzed decarboxylative cross-coupling of oxazoles and thiazoles with α-oxocarboxylic acids was developed through an sp2 C-H bond functionalization process. This work represents the first example of cobalt-catalyzed decarboxylative C-H
Synthesis of 2-Acylbenzothiazoles via the Cu(OTf)2-Catalyzed tandem reaction of β,β-Dihalidestyrenes with 2,2′- Disulfanediyldianilines
Zhou, Zeng-Le,Fang, Tao,Tang, Ri-Yuan,Zhang, Xing-Guo,Deng, Chen-Liang
supporting information, p. 255 - 260 (2014/02/14)
A new method has been developed for the one-pot construction of 2-acylbenzothiazoles via the Cu(OTf)2-catalyzed tandem reaction of β,β-dihalidestyrenes with 2,2′-disulfane-diyldianilines. A variety of different dihalidestyrenes and diphenyldisulfanes were efficiently converted into the corresponding 2-acylbenzothiszole derivatives in the presence of Cu(OTf)2. Most importantly, this protocol allowed for the long chain 1,1-dibromohept-1-ene to be converted into the corresponding 2-hexylbenzo[d]thiazole in moderate yield. Georg Thieme Verlag Stuttgart, New York.
A one-pot hypoiodite catalysed oxidative cycloetherification approach to benzoxazoles
Boominathan, Siva Senthil Kumar,Hu, Wan-Ping,Senadi, Gopal Chandru,Vandavasi, Jaya Kishore,Wang, Jeh-Jeng
supporting information, p. 6726 - 6728 (2014/06/23)
A practical one-pot hypoiodite catalysed oxidative cyclization approach to synthesize α-ketobenzoxazole derivatives was successfully developed. This operationally simple protocol utilizes easily-accessible starting materials and has a broad substrate scope with excellent yields. This journal is the Partner Organisations 2014.
