885-34-7Relevant academic research and scientific papers
Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines
Garia, Alankrita,Grover, Jatin,Jain, Nidhi
, p. 4125 - 4131 (2021/08/24)
Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.
Practical Synthesis of Benzimidazo[1,2- A[quinolines via Rh(III)-Catalyzed C-H Activation Cascade Reaction from Imidamides and Anthranils
Hu, Yao,Wang, Ting,Liu, Yanzhao,Nie, Ruifang,Yang, Ninghong,Wang, Qiantao,Li, Guo-Bo,Wu, Yong
supporting information, p. 501 - 504 (2020/01/31)
We report a novel and practical one-pot Rh(III)-catalyzed strategy to construct benzimidazo[1,2-a]quinolines from readily available imidamides and anthranils. The cascade reaction proceeds via a C-H amination-cyclization-cyclization process in ionic liquid without any additives and possesses simple operation, moderate-to-high yield, and broad substrate scope features, which will provide the reference for the construction of biologically active fused benzimidazoles.
Synthesis of 3-phenylbenzo[c]isoxazoles by thermocyclization of 2-azidobenzophenones
Odinokov,Plekhovich,Budruev
, p. 1298 - 1300 (2019/07/15)
3-Phenylbenzo[c]isoxazoles were synthesized by non-catalytic thermolysis of 2-azidobenzophenones in dry xylene with quantitative yields. The trace content of water in solvents reduces the yields of the reaction products. 2-Azidobenzoic acid esters are sta
Mechanism of formation of 2,1-benzisoxazoles in reactions of nitroarenes with arylacetonitriles
Orlov,Kotov,Tsivov,Rusakov
, p. 245 - 252 (2015/04/14)
Main regularities in reactions of arylacetonitriles with nitroarenes were discussed. The reaction mechanism has been suggested proceeding from the experimental data and the quantum chemical modeling of the limiting stage, the formation of the 2,1-benzisoxazole ring.
Synthesis and properties of diarylamino-substituted linear and dendritic oligoquinolines for organic light-emitting diodes
Lee, Ho-Joon,Xin, Hao,Park, Seong-Min,Park, Seog-IL,Ahn, Taek,Park, Dong-Kyu,Jenekhe, Samson A.,Kwon, Tae-Woo
experimental part, p. 1627 - 1637 (2012/07/16)
The coupling reaction between 5-bromo-3-phenylbenzo[c]isoxazole and diphenylamine followed by further condensation with a mono-, di- or ter-acetyl aromatic compound in the presence of diphenyl phosphate at 145 oC gave a novel asymmetric diarylquinolines, oligoquinolines with diphenylamine endgroups, and a first generation quinoline dendrimer in 41-82% isolated yield. The electrochemical and photophysical properties of the oligoquinolines were characterized by cyclic voltammograms (CVs) and spectroscopy. All the quinolines emit bright sky blue light due to charge transfer from quinoline group to diphenly amine with very high quantum efficiency (> 90%). Organic light-emitting diodes (OLEDs) were fabricated using these quinolines as emitting materials. Among different device architectures explored, OLEDs with a structure of ITO/PEDOT (40 nm)/TAPC (15 nm)/D-A quinoline (40 nm)/TPBI (30 nm)/LiF (1 nm)/Al using TAPC as an electron blocking layer and TPBI as a hole blocking layer gave the best performance. A high external quantum efficiency in the range of 1.2-2.3% were achieved in all the quinolines with the best performance in BBQA(5). Our results indicate diarylamino-substituted oligoquinoline and dendrimer are promising materials for OLEDs applications.
QUINOLINE, NAPHTHALENE AND CONFORMATIONALLY CONSTRAINED QUINOLINE OR NAPHTHALENE DERIVATES AS ANTI-MYCOBACTERIAL AGENTS
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Page/Page column 48, (2009/08/16)
The invention relates to a compound of general formula I, II, III, IV V VI, VII, VIII, IX, X or a tautomer and the stereochemically isomeric forms thereof or pharmaceutically acceptable salts thereof, a N-oxide form thereof or a pro-drug thereof. The compound is usable as a medicament for the treatment of mycobacterial disease
Synthesis of substituted 2-pyridyl-4-phenylquinolines
Mamo, Antonino,Nicoletti, Salvatore,Tat, N. Cam
, p. 618 - 627 (2007/10/03)
The acid-catalyzed condensation of o-aminobenzophenones with aromatic acetyl derivatives, in a basic methanol/tetrahydrofuran medium, has been used to prepare a series of substituted 2-pyridyl-4-phenylquinolines. Derivatives having two aza binding sites can act as asymmetric bidendate ligands to complex transition metals such as ruthenium, osmium or iridium. All the compounds were characterized by elemental analysis, Ei or FAB (+) MS, 1H- and 13C-NMR spectroscopies. Complete assignments of the (1)H spectra were accomplished by using a combination of one- and two-dimensional NMR techniques.
Nucleophilic replacement of hydrogen in para-substituted nitrobenzenes by phenylacetonitrile carbanion
Orlov,Sokovikov,Kotov
, p. 100 - 103 (2007/10/03)
The kinetic relations holding in nucleophilic replacement of hydrogen in para-substituted nitrobenzenes by phenylacetonitrile carbanion suggest a complex reaction mechanism involving two alternative pathways. The direction of the process is determined by the structure of intermediate σ-complex.
Nucleophilic substitution of hydrogen in activated nitroarenes by phenylacetonitrile carbanion
Orlov,Sokovikov,Kotov,Starikov
, p. 1735 - 1738 (2007/10/03)
General relations holding in nucleophilic substitution of hydrogen in para-substituted nitroarenes by phenylacetonitrile carbanion were analyzed in terms of the Klopman reactivity indices. Requirements to the substrate structure were determined, which restrict the scope of application of this method to synthesis of 2,1-benzisoxazole derivatives.
