70216-32-9Relevant academic research and scientific papers
Pd/Cu-Catalyzed C-H/C-H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates
Lin, Zeng-Hui,Tian, Ze-Yu,Zhang, Cheng-Pan
supporting information, p. 4400 - 4405 (2021/06/27)
A highly efficient method for the selective formal C-H/C-H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity, one-pot procedures, and the late-stage functionalization of complex molecules without the use of oxidants, offering a promising strategy for the transition-metal-catalyzed C-H arylation of azoles.
Synthesis of 2,5-diaryloxazoles through rhodium-catalyzed annulation of triazoles and aldehydes
Li, Jian,Liu, Li,Lu, Xue-Chen,Wang, Zheng-Bing,Xu, De-Feng,Xu, Yue,Zhu, Shang-Rong
, p. 24795 - 24799 (2020/07/14)
An efficient synthesis of a variety of 2,5-diaryloxazole derivatives via a rhodium-catalyzed annulation of triazoles and aldehydes is achieved. Various oxazole derivatives could be obtained in good to excellent yields. A concise synthesis of antimycobaterial natural products balsoxin and texamine has been achieved using this method. This journal is
Synthesis method of oxazole heterocyclic compound
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Paragraph 0016; 0047-0048, (2020/04/17)
The invention belongs to the technical field of organic synthesis and medicines, and particularly relates to a synthesis method of an oxazole heterocyclic compound. Aryl aldehyde and a triazole derivative are used as raw materials and are heated to react in the presence of trichloromethane and rhodium acetate catalysts to obtain the oxazole heterocyclic compound. By using the method provided by the invention, under the condition of heating and stirring, the oxazole heterocyclic derivative can be obtained at a relatively high yield after reaction for 3-12 hours. According to the method disclosed by the invention, the oxazole heterocyclic derivative is simply, conveniently and efficiently synthesized by using simple and easily available raw materials through a one-step method, and a simple and efficient new synthesis method with wide substrate universality is provided for synthesizing the oxazole heterocyclic derivative.
CO2/Photoredox-Cocatalyzed Tandem Oxidative Cyclization of α-Bromo Ketones and Amines to Construct Substituted Oxazoles
Zhang, Xiaowei,He, Yonghui,Li, Jing,Wang, Rui,Gu, Lijun,Li, Ganpeng
, p. 8225 - 8231 (2019/06/17)
CO2/photoredox-cocatalyzed tandem oxidative cyclization of α-bromo ketones and amines for the preparation of substituted oxazoles has been achieved. The avoidance of using both transition-metal catalysts and peroxides makes this method more sustainable and renewable.
Synthesis of 2,5-disubstituted oxazoles: Via cobalt(III)-catalyzed cross-coupling of N -pivaloyloxyamides and alkynes
Yu, Xiaolong,Chen, Kehao,Wang, Qi,Zhang, Wenjing,Zhu, Jin
supporting information, p. 1197 - 1200 (2018/02/09)
An efficient synthesis of 2,5-disubstituted oxazoles via Co(iii) catalysis is described herein. The synthesis is achieved under mild conditions through [3+2] cycloaddition of N-pivaloyloxyamides and alkynes. The reaction operates through an internal oxidation pathway and features a very broad substrate scope. The one-step synthesis of natural products such as texamine and balsoxin has been demonstrated via this protocol.
Unprecedented salt-promoted direct arylation of acidic sp2 C[sbnd]H bonds under heterogeneous Ni-MOF-74 catalysis: Synthesis of bioactive azole derivatives
Nguyen, Huong T.T.,Doan, Duc N.A.,Truong, Thanh
, p. 141 - 149 (2016/12/09)
Herein, nickel-based metal-organic framework, Ni-MOF-74, was synthesized by a solvothermal method and its properties was characterized by a host of techniques. Ni-MOF-74 exhibited exceptional catalytic activity toward the direct arylation of azoles via C[sbnd]H activation while other Ni-MOFs, nickel-based heterogeneous systems, and homogeneous counter parts displayed lower activity. Optimal conditions involved the use of Li2CO3 or KCl salts in diglyme solvent in 18 h and no additional ligand is required. This is the first and unprecedented report using KCl salt as promoter for arylation of heterocycles. By avoiding the use of strong bases and oxidants, optimized conditions are compatible with wide range of functional groups and heterocycles. Furthermore, by taking advantage of large aperture size of Ni-MOF-74, we are able to utilize optimized conditions to successfully synthesize several bioactive arylated azole derivatives. Previous studies using heterogeneous catalysts to approach these bioactive compounds are not performed in the literature. Leaching tests indicated that homogeneous catalysis via leached active nickel species is unlikely. Thus, the catalyst was facilely separated from the reaction mixture and reused several times without significant degradation of the catalytic reactivity.
Photoinduced Copper-Catalyzed C-H Arylation at Room Temperature
Yang, Fanzhi,Koeller, Julian,Ackermann, Lutz
supporting information, p. 4759 - 4762 (2016/04/19)
Room-temperature azole C-H arylations were accomplished with inexpensive copper(I) compounds by means of photoinduced catalysis. The expedient copper catalysis set the stage for site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine. Copper light: Room-temperature C-H arylations of heteroarenes were accomplished with inexpensive copper compounds by photoinduced catalysis. The expedient copper catalysis leads to site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine.
Metal-Free sp3 C-H Functionalization: PABS/I2-Promoted Synthesis of Polysubstituted Oxazole Derivatives from Arylethanones and 2-Amino-2-alkyl/arylacetic Acid
Hu, Ting,Yan, Hao,Liu, Xingxing,Wu, Chaoyang,Fan, Yuxing,Huang, Jing,Huang, Guosheng
supporting information, p. 2866 - 2869 (2015/12/18)
A nonmetal-catalyzed process for the synthesis of polysubstituted oxazoles from inexpensive and readily available α-amino acids and methyl ketones is established. This reaction is proposed to achieve oxidative cleavage of C(sp3)-H bonds, followed by decarboxylation and annulation. The mild reaction conditions employed in both cases enable the tolerance of a wide range of functional groups as well as high reaction efficiency.
One-pot total synthesis: The first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners from amino acids
Xiang, Jiachen,Wang, Jungang,Wang, Miao,Meng, Xianggao,Wu, Anxin
supporting information, p. 7470 - 7475 (2014/12/10)
In this work, we accomplished the first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners: pimprinine, pimprinethine, pimprinaphine, WS-30581A, WS-30581B, laboradorin 1, uguenenazole, balsoxine, texamine in one-pot from commercially available starting materials including amino acids. Further investigating into the mechanism revealed that this improved transformation was achieved by the integration of iodination, Kornblum oxidation, condensation, decarboxylation, annulation, and oxidation reaction sequence.
Synthesis and evaluation of photophysical properties of Series of π-conjugated oxazole dyes
Mahuteau-Betzer, Florence,Piguel, Sandrine
, p. 3188 - 3193 (2013/06/27)
Incorporation of π-conjugated spacers at the 2 or 5 position of a 2,5-disubstitutedaryloxazole led to new series of fluorescent dyes. They show emissions from visible to 700 nm along with significant Stokes shift up to 208 nm and a strong solvatochromic fluorescence. These compounds are easily accessible in one step through direct C-H bond functionalization.
