33757-48-1Relevant articles and documents
Site-specific: Ortho metallation via C-H bond activation and syntheses of ruthenium(III) organometallics: Studies on nitric oxide (NO) reactivity and photorelease of coordinated NO
Kumar, Rajan,Kumar, Sushil,Bala, Manju,Ratnam, Anand,Singh,Ghosh, Kaushik
, p. 72096 - 72106 (2016)
A new family of σ-aryl ruthenium(iii) complexes [Ru(L1-4)(PPh3)2Cl] (1-4) (where L1H2 = N-(quinolin-8-yl)benzamide for 1, L2H2 = 4-chloro-N-(quinolin-8-yl)benzamide for 2, L3H2 = 4-nitro-N-(quinolin-8-yl)benzamide for 3, L4H2 = 3-nitro-N-(quinolin-8-yl)benzamide for 4 and H = dissociable protons) derived from bidentate ligands having amide bonds was synthesized through C-H bond activation. These organometallic ruthenium(iii) complexes were treated with nitric oxide (NO) to afford the nitrosyl complexes [Ru(NO2L1-4)(PPh3)2(NO)](ClO4) (1a-4a) (where NO2L1H2 = N-(5-nitroquinolin-8-yl)benzamide for 1a, NO2L2H2 = 4-chloro-N-(5-nitroquinolin-8-yl)benzamide for 2a, NO2L3H2 = 4-nitro-N-(5-nitroquinolin-8-yl)benzamide for 3a, NO2L4H2 = 3-nitro-N-(5-nitroquinolin-8-yl)benzamide for 4a and H = dissociable protons). All ruthenium complexes were characterized by various spectroscopic techniques. An X-ray crystallographic study afforded the molecular structure of complex 4a and the site-specific orthometallation was scrutinized. The coordinated NO molecule was found to be photolabile under visible and UV light.
Copper-Catalyzed Formal [4 + 1] Cycloaddition of Benzamides and Isonitriles via Directed C-H Cleavage
Takamatsu, Kazutaka,Hirano, Koji,Miura, Masahiro
, p. 4066 - 4069 (2015)
A copper-catalyzed formal [4 + 1] cycloaddition of benzamides and isonitriles via 8-aminoquinoline-directed C-H cleavage has been developed. The reaction proceeds well even in the presence of a base metal catalyst, CuBr·SMe2, alone to deliver the corresponding 3-iminoisoindolinones in good yields. Moreover, the unique acceleration effects of diphenyl sulfide are also disclosed.
Palladium-Catalyzed ortho-Selective C-H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions
Konishi, Miki,Tsuchida, Kazuya,Sano, Katsuya,Kochi, Takuya,Kakiuchi, Fumitoshi
, p. 8716 - 8724 (2017)
The palladium-catalyzed ortho-selective chlorination of N-quinolinylbenzamide derivatives with hydrochloric acid was achieved under anodic oxidation conditions. The use of 5,7-dichloro-8-quinolinyl group as directing group was effective for the selective
Copper(I)-Catalyzed Sulfonylation of 8-Aminoquinoline Amides with Sulfonyl Chlorides in Air
Qiao, Huijie,Sun, Suyan,Yang, Fan,Zhu, Yu,Zhu, Weiguo,Dong, Yaxi,Wu, Yusheng,Kong, Xiangtao,Jiang, Ling,Wu, Yangjie
, p. 6086 - 6089 (2015)
A simple and mild protocol for copper(I)-mediated sulfonylation of 8-aminoquinoline amides with sulfonyl chlorides was developed, affording desired products in moderate to good yields. This reaction proceeds in air and features excellent substrate tolerance, especially for aliphatic sulfonyl chlorides.
Nickel-mediated C(sp2)-H amidation in synthesis of secondary sulfonamides via sulfonyl azides as amino source
Xu, Peng,Ding, Peng-Fei,Zhang, Mei-Qi,Xia, Yu-Shi,Xie, Ting
, (2021/02/16)
In this paper, Ni(II)- Catalyzed ortho-amidation of C(sp2)-H bond with sulfonyl azides directed by (quinolin-8-yl) amine (AQ-amine) is described. The method provides a straightforward method for the synthesis of sulfonamides from available sulfonyl azides via the transition-metal-catalyzed C(sp2)-N bond forming reaction. The amidation reactions exhibit high functional group compatibility, which might proceed a Ni(III)/Ni(I) catalytic cycle. We also applied sulfonamide compound in OLEDs, which exhibits the certain application potential in OLEDs field.
Aryne Multicomponent Reactions by Directed C?H Activation
Sunnam, Sunil Kumar,Belani, Jitendra D.
, p. 8846 - 8850 (2021/05/31)
Arylation via ortho C?H activation by the aid of directing groups has been explored recently by many researchers. Herein, a palladium-catalyzed C?H arylation using 8-aminoquinoline as a bidentate directing group has been developed. The reaction furnishes only C?H arylation, unlike previous methods where cyclization to corresponding isoquinolones is observed. More interestingly, sequential C?H functionalization was observed when methylacrylate and acrylonitrile was added; this led to C?H olefination with the aryl group, which was installed from the aryne precursor.
Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides
Chen, Xi,Ding, Ya-Nan,Gou, Xue-Ya,Liang, Yong-Min,Luan, Yu-Yong,Niu, Zhi-Jie,Shi, Wei-Yu,Zhang, Zhe,Zheng, Nian
, p. 8945 - 8948 (2021/09/10)
C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.
Transition Metal-Free Regioselective Remote C?H Bond 2,2,2-Trifluoroethoxylation of 8-Aminoquinoline Derivatives at the C5 Position
Ruyet, Louise,Poisson, Thomas,Besset, Tatiana
supporting information, p. 3407 - 3410 (2021/06/28)
The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-aminoquinoline has been developed. In the presence of PIDA, an unprecedented and undirected transition metal-free transformation was achieved using the readily available and appealing 2,2,2-trifluoroethanol as the fluorinated source. The selective distal 2,2,2-trifluoroethoxylation of an array of amides was achieved in moderate to good yields (12 examples, up to 61 % yield). This approach provided efficient access to high-value added fluorinated quinoline derivatives, key building blocks for bulk and fine chemical industry.
Erratum: Catalytically Relevant Intermediates in the Ni-Catalyzed C(sp2)-H and C(sp3)-H Functionalization of Aminoquinoline Substrates (J. Am. Chem. Soc. (2019) 141:43 (17382-17387) DOI: 10.1021/jacs.9b09109)
Bour, James R.,Kampf, Jeff W.,Roy, Pronay,Sanford, Melanie S.
supporting information, p. 14021 - 14021 (2021/09/08)
Further analysis of our data revealed that the thermolysis ofNi(III) complex 4b does not lead to C(sp3)-N bondformingreductive elimination to form ?-lactam 3b-H. As such, our claim that this is “the first directly observable example of C(sp3)-N coupling from an isolated NiIII center” is incorrect. Equation 6 should be modified as follows: As a consequence, the statement in the Abstract that “a NiIII s-alkyl analogue underwent C(sp3)-N bond-forming reductive elimination at 140 °C in DMF to afford a ?-lactam product” is also incorrect. The TOC graphic should also be corrected as follows: After the discovery of this major error, we went back and carefully repeated all of the synthesis and reactivity experiments described in the Article to ensure their accuracy and reproducibility. This has led to changes in the yields and in some cases solvent and reaction time for many of the reactions reported therein. The Supporting Information has been updated with revised procedures and spectra as well as updated yields. In addition, we have included in the revised Supporting Information a copy of an updated manuscript with each change highlighted to clearly indicate these revisions. Unlike the error in eq 6, none of these additional changes alters our key conclusions from the original manuscript.FF
C-H Amidation and Amination of Arenes and Heteroarenes with Amide and Amine using Cu-MnO as a Reusable Catalyst under Mild Conditions
Singh, Harshvardhan,Sen, Chiranjit,Suresh, Eringathodi,Panda, Asit B.,Ghosh, Subhash C.
, p. 3261 - 3275 (2021/02/16)
An atom-economical and efficient route for the direct amidation and amination of aryl C-H bonds using our synthesized recyclable heterogeneous Cu-MnO catalyst is reported here. The direct C-H amidation was carried out using a simple amide without any prea
