cas 41420-90-0, 2-(4-bromophenyl)-1,3,4-oxadiazole

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Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds
The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.
Chang, Xiao-Yong,Chen, Ji-Jun,Gu, Qiang-Shuai,Jiang, Sheng-Peng,Li, Zhong-Liang,Liu, Lin,Liu, Xiao-Dong,Liu, Xin-Yuan,Su, Xiao-Long,Wang, Fu-Li,Yang, Chang-Jiang,Ye, Liu
supporting information
p. 380 - 384
(2020/10/30)

[4u202f+u202f1] Cyclization of benzohydrazide and ClCF2COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5
A facile synthesis of 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5 via [4 + 1] cyclization of ClCF2COONa with non-amine compounds containing amino groups is developed. Of note, this is the first time that halofluorinated compounds are used as C1 synthon to construct deuterated nitrogen-heterocyclic compounds. The current protocol features simple operation, readily accessible raw materials, wide substrate scope and valuable products
Li, Xin,Mu, Shiqiang,Song, Qiuling,Wang, Ya
supporting information

(2021/09/20)

Ligand-Enabled Palladium-Catalyzed Through-Space C?H Bond Activation via a Carbopalladation/1,4-Pd Migration/C?H Functionalization Sequence
We report, herein, a palladium-catalyzed cascade comprising carbopalladation, 1,4-Pd-migration and C(sp2)?C(sp2) bond formation to construct a variety of bis-heterocyclic frameworks in a single operational step. The methodology provi
Chen, Su,Ranjan, Prabhat,Ramkumar, Nagarajan,Van Meervelt, Luc,Van der Eycken, Erik V.,Sharma, Upendra K.
supporting information
p. 14075 - 14079
(2020/10/12)

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE
Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.
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Paragraph 002028; 002029

(2021/01/22)

Method for constructing 2-(4-bromophenyl)-1,3,4-oxadiazole by one step through DMF as carbon source
The invention discloses a method for constructing 2-(4-bromophenyl)-1,3,4-oxadiazole by one step through DMF(N,N-dimethylformamide) as a carbon source. The method is characterized in that bromobenzhydrazide is used as a reaction raw material, DMF(N,N-dime
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Paragraph 0016

(2019/02/03)

DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles
An unprecedented Cu-catalyzed direct annulation of hydrazides with N,N-dimethylformamide (DMF) was developed, providing an efficient synthesis of valuable 1,3,4-oxadiazoles. This process features the short reaction time and can be safely conducted on gram scale. The reaction also facilitated the convenient synthesis of 1,3,4-oxadiazole-2(3H)-ones. Moreover, the mechanistic studies suggest that the source of CH is from the N-methyl group of DMF. (Figure presented.).
Wang, Shoucai,Wang, Kai,Kong, Xiangfei,Zhang, Shuhua,Jiang, Guangbin,Ji, Fanghua
supporting information
p. 3986 - 3990
(2019/07/31)

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE
Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.
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Paragraph 002070; 002071; 002072

(2019/07/17)

Aromatic compound and organic electroluminescent device thereof
The invention provides an aromatic compound and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. The aromatic compound has a high glass transition temperature, very high electron transmission ability, good stability and high film forming ability, has proper HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) values, is used as an electron transmission layer in OLED (Organic Light-Emitting Diode) devices, can effectively reduce the driving voltage of a device, improve the luminous efficiencyand brightness of the device, and prolong the service life of the device, and is a kind of organic electroluminescent material with excellent performance.
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Paragraph 0074; 0075; 0077

(2019/01/08)

Synthesis of 1,3,4-Oxadiazoles via Annulation of Hydrazides and Benzene-1,3,5-triyl Triformate under Metal-Free Conditions
A new and efficient method for the synthesis of 1,3,4-oxadiazoles via the annulation of hydrazides with benzene-1,3,5-triyl triformate (TFBen) under metal-free conditions is reported. A broad range of hydrazides were transformed into the corresponding 1,3
Yin, Zhiping,Power, Dennis J.,Wang, Zechao,Stewart, Scott G.,Wu, Xiao-Feng
supporting information
p. 3238 - 3242
(2018/04/24)

Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp2)-H or C(sp)-H Bond
An I2-promoted, metal-free domino protocol for one-pot synthesis of 1,3,4-oxadiazoles has been developed via oxidative cleavage of C(sp2)-H or C(sp)-H bonds, followed by cyclization and deacylation. In this reaction, the use of K2CO3 as a base is found to be an essential factor in the cyclization and the C-C bond cleavage. This procedure proceeded smoothly in moderate to high yields with good functional group compatibility.
Fan, Yuxing,He, Yongqin,Liu, Xingxing,Hu, Ting,Ma, Haojie,Yang, Xiaodong,Luo, Xinliang,Huang, Guosheng
p. 6820 - 6825
(2016/08/16)

Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones
A new strategy for the synthesis of 1,3,4-oxadiazoles was established through direct annulation of hydrazides with methyl ketones. It was found that the use of K2CO3 as a base achieves an unexpected and highly efficient C-C bond clea
Gao, Qinghe,Liu, Shan,Wu, Xia,Zhang, Jingjing,Wu, Anxin
supporting information
p. 2960 - 2963
(2015/06/30)

Microwave promoted one-pot synthesis of 2-aryl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazole derivatives using Al3+-K10 clay as a heterogeneous catalyst
An efficient, inexpensive method is developed for the one-pot synthesis of 2-aryl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazoles starting from acid hydrazides and trimethyl orthoformate under solvent-free, microwave conditions using a reusable Alsup
Suresh, Dhanusu,Kanagaraj, Kuppusamy,Pitchumani, Kasi
supporting information
p. 3678 - 3682
(2014/06/23)

Novel, fast and efficient one-pot sonochemical synthesis of 2-aryl-1,3,4-oxadiazoles
Ultrasound promoted synthesis of 2-aryl-1,3,4-oxadiazoles at ambient temperature is reported. The remarkable features of the new procedure are shorter reaction time, excellent yields, cleaner reaction profile and simple experimental and workup procedure.
Rouhani, Morteza,Ramazani, Ali,Joo, Sang Woo
p. 262 - 267
(2013/10/01)

Room-temperature copper-catalyzed oxidation of electron-deficient arenes and heteroarenes using air
No pressure: The oxidation of aromatic C-H bonds at room temperature was realized through a copper-catalyzed "oxygenase-type" oxidation of arenes and heteroarenes in the presence of air (see scheme). The reaction involves an oxygen-atom transfer from O2 in the air onto the substrates. Copyright
Liu, Qiang,Wu, Pan,Yang, Yuhong,Zeng, Ziqi,Liu, Jie,Yi, Hong,Lei, Aiwen
supporting information; experimental part
p. 4666 - 4670
(2012/06/30)

17O NMR studies of substituted 1,3,4-oxadiazoles
Three series of substituted 1,3,4-oxadiazoles were studied by 17O NMR spectroscopy. Chemical shifts values were correlated with empirical Hammett parameters as well as calculated bond lengths and chemical shielding values.
Gierczyk, Blazej,Zalas, MacIej,Kazmierczak, Marcin,Grajewski, Jakub,Pankiewicz, Radoslaw,Wyrzykiewicz, Bozena
scheme or table
p. 648 - 654
(2012/01/06)

Carbon dioxide as the C1 source for direct C-H functionalization of aromatic heterocycles
(Equation Presented). A simple and straightforward method has been developed for the direct carboxylation of aromatic heterocylces such as oxazoles, thiazoles, and oxadiazoles using CO2 as the C1 source. The reactions require no metal catalyst and only Cs2CO3 as the base. A good functional group tolerance is achieved.
Vechorkin, Oleg,Hirt, Nathalie,Hu, Xile
supporting information; experimental part
p. 3567 - 3569
(2010/10/02)

NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
The present invention provides a novel phenylpropionic acid derivative and a PPAR-γ modulator comprising the same as an active ingredient. The phenylpropionic acid derivative of the present invention has modulatory action on function of PPAR-γ and then exhibits hypoglycemic, hypolipidemic and insulin resistance-reducing effects on PPAR-mediated diseases or disorders. Therefore, the present invention is prophylactically or therapeutically effective for diabetes and metabolic diseases.
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Page/Page column 37

(2010/04/23)

NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
The present invention provides a novel phenylpropionic acid derivative and a PPAR-γ modulator comprising the same as an active ingredient. The phenylpropionic acid derivative of the present invention has modulatory action on function of PPAR-γ and then exhibits hypoglycemic, hypolipidemic and insulin resistance-reducing effects on PPAR-mediated diseases or disorders. Therefore, the present invention is prophylactically or therapeutically effective for diabetes and metabolic diseases.
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(2008/12/08)

ETHANOLAMINE SALT OF N- (3-METHOXY-5-METHYLPYRAZIN-2YL) -2- (4- [1 , 3 , 4-0XADIAZ0LE-2-YL] PHENYL) PYRIDINE-3- SULPHONAMIDE
N-(Methoxy-5-methylpyrazin-2-yl)-2-(4-[1 ,3,4-oxadiazol-yl]phenyl)pyridine-3- sulphonamide ethanolamine salt its synthesis and its uses are described.
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Page/Page column 32

(2010/11/25)

The reaction of (N-isocyanimino)triphenylphosphorane with benzoic acid derivatives: a novel synthesis of 2-aryl-1,3,4-oxadiazole derivatives
The reactions of benzoic acid derivatives with (N-isocyanimino)triphenylphosphorane proceed smoothly at room temperature to afford 2-aryl-1,3,4-oxadiazoles in high yields.
Souldozi, Ali,Ramazani, Ali
p. 1549 - 1551
(2008/02/03)

CHEMICAL PROCESS
Process for preparing compounds of Formula (I); and (IV); are described.
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Page/Page column 11

(2008/06/13)

Characterization of 2-aryl-1,3,4-oxadiazoles by 15N and 13C NMR spectroscopy
15N NMR chemical shifts of 2-aryl-1,3,4-oxadiazoles were assigned on the basis of the 1H-15N HMBC experiment. Chemical shifts of the nitrogen and carbon atoms in the oxadiazole ring correlate with the Hammett σ-constants of substituents in the aryl ring (r2 ≥ 0.966 for N atoms). 15N NMR data are a suitable and sensitive means for characterizing long-range electronic substituent effects. Additionally, 13C NMR data for these compounds are presented. Copyright
Nowak-Wydra, Barbara,Gierczyk, Blazej,Schroeder, Grzegorz
p. 689 - 692
(2007/10/03)