Category: 2343-22-8

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of 5- and 6-haloindoles from indoline》. Authors are Ikan, R.; Hoffmann, E.; Bergmann, E. D.; Galun, A..The article about the compound:5-Fluoroindolinecas:2343-22-8,SMILESS:FC1=CC2=C(NCC2)C=C1).Quality Control of 5-Fluoroindoline. Through the article, more information about this compound (cas:2343-22-8) is conveyed.

cf. Terent’ev, et al., CA 54, 10991c. A mixture of 240 g. indoline and 2 1. concentrated H2SO4 stirred 1 hr. below 0° with a mixture of 90 ml. HNO3 and 2 h H2SO4 gave 95% 6-nitroindoline, m. 66-7° (BuOH); NAc derivative (I) m. 156-7°. I (250 g.) suspended in 600 ml. isoPrOH and hydrogenated over 10% Pd-C at 70°/80 lb./in.2 gave 85% 6-amino-1-acetyfindole (II), m. 181°. II (500 g.) suspended in a mixture of 760 ml. H2O and 760 ml. concentrated HCl and diazotized at 0-5° by a solution of 208 g. NaNO2 in 420 H2O, gave on stirring 1 hr. at 0-5° with a solution of 580 g. NaBF4 in 1 1. H2O a diazonium salt, which, filtered and washed successively with aqueous NaBF4 solution, cold EtOH, and Et2O and then dried, was extracted with iso-PrOH to give 55% 6-fluoro-1-acetylindole (III), b1 180°, b0.5 165°, m. 79-80°. III refluxed 1 hr. with 10 parts concentrated HCl gave quant. 6-fluoroindoline (IV), b0.3 70-2°, n29D 1.5533, also obtained directly by adding 1.5 moles NaOH/mole II to the iso-PrOH extract of the decomposition product of the diazonium fluoborate, and subsequent distillation A mixture of 7 1. xylene, 470 g. chloranil, and 194 g. IV refluxed 5 hrs. gave 60% 6-fluoroindole (V), m. 74.5-5.5°. IV (50 g.) dehydrogenated by 20-min. treatment at 180-200° with 3 g. 10% Pd-C gave 35% V. Dropwise addition of 170 ml. fuming HNO3 to 220 g. indoline in 3 1. Ac2O at 10-12° gave 350 g. orange solid when the product was poured on ice. After removing the small amount of dinitroacetylindoline by refluxing the product with 10 parts concentrated HCl 1 hr. and then filtering off the more acidic dinitroindole which precipitated, the filtrate was made alk. to aqueous NaOH solution and the precipitate refluxed 3 hrs. with Ac2O to give 73% 5-nitro-1-acetylindoline, m. 175-6° (AcOH), which hydrogenated over 10% Pd-C at 70° gave 85% the 5-amino analog (VI), m. 185-6° (aqueous EtOH). VI, diazotized and subjected to a Schiemann reaction, gave 55% 5-fluoro-1-acetylindoline, b8 170°, m. 110-11°, which was deacetylated quant. to 5-fluoroindoline, b15 116-18°, n24D 1.5559, and converted into 5-fluoroindole, m. 45-6°, by the above method. II (176 g.) was suspended in a mixture of 250 ml. H2O and 250 ml. concentrated HCl and diazotized at 0° with a solution of 70 g. NaNO2 in 150 ml. H2O, and the resulting diazonium solution added slowly at 0° to a Cu2Cl2. solution prepared from 310 g. CuSO4.5H2O and 81 g. NaCl in 1 1. H2O, 66 g. NaHSO3 and 44 g. NaOH in 0.5 1. H2O, and 500 ml. concentrated HCl, and the mixture heated to 45° slowly, stirred 2 hrs., cooled to 0°, and filtered gave 56% 6-chloro-1-acetylindoline, m. 127-8°, 85 g. of which refluxed 1 hr. with 850 ml. concentrated HCl gave 6-chloroindoline-HCl, m. 210°; the free base (VII) b28 156-8°, n29D 1.5984. Dehydrogenated with chloranil VII gave 60% 6-chloroindole, m. 89-90°. Similarly, 5-amino-1-acetylindoline gave 60%, the 5-chloro analog, m. 115-16° (EtOH), which was deacetylated to 94% 5-chloroindoline, b20 132-5°, n24D 1.5996, and in turn dehydrogenated to 62% 5-chloroindole, m. 69-70°, by chloranil. Ultraviolet data for these compounds were given.

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Related Products of 2343-22-8. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-Fluoroindoline, is researched, Molecular C8H8FN, CAS is 2343-22-8, about Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles. Author is Huang, Honggui; Yu, Menglin; Su, Xiaolong; Guo, Peng; Zhao, Jia; Zhou, Jiabing; Li, Yi.

We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.

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Recommanded Product: 5-Fluoroindoline. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5-Fluoroindoline, is researched, Molecular C8H8FN, CAS is 2343-22-8, about B(C6F5)3-promoted hydrogenations of N-heterocycles with ammonia borane. Author is Ding, Fangwei; Zhang, Yiliang; Zhao, Rong; Jiang, Yanqiu; Bao, Robert Li-Yuan; Lin, Kaifeng; Shi, Lei.

A transition-metal-free method for the B(C6F5)3-promoted hydrogenations of N-heterocycles using ammonia borane under mild reaction conditions was developed. The reaction afforded a broad range of hydrogenated products in moderate to good yields. The enantioselective versions for the corresponding products were also investigated via our approach, showing good feasibility.

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Application of 2343-22-8. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Fluoroindoline, is researched, Molecular C8H8FN, CAS is 2343-22-8, about Identification of benzo[d]pyrrolo[2,1-b]thiazole derivatives as CENP-E inhibitors. Author is Yamane, Masayoshi; Sawada, Jun-ichi; Ogo, Naohisa; Ohba, Mai; Ando, Takayuki; Asai, Akira.

Kinesin centromere-associated protein E (CENP-E) has emerged as a potential target for the development of anticancer drugs due to its involvement in the mitotic progression of the cell cycle. Although several CENP-E inhibitors have been reported, more knowledge of chem. structures and inhibitory mechanisms is necessary for developing CENP-E inhibitors. Here, we describe the identification of new CENP-E inhibitors. Screening of a small-mol. chem. library identified benzo[d]pyrrolo[2,1-b]thiazole derivatives, including 1, as compounds with inhibitory activity against the microtubule-stimulated ATPase of the CENP-E motor domain. Among the mitotic kinesins examined, 1 selectively inhibited the kinesin ATPase activity of CENP-E. In a steady-state ATPase assay, 1 exhibited ATP-competitive behavior, which was different from the CENP-E inhibitor GSK923295. Compound 1 inhibited the proliferation of tumor-derived HeLa and HCT116 cells more efficiently than that of non-cancerous WI-38 cells. The inhibition of cell proliferation was attributed to the ability of 1 to induce apoptotic cell death. The compound showed antimitotic activity, which caused cell cycle arrest at mitosis via interference with proper chromosome alignment. We identified 1 and its derivatives as the lead compounds that target CENP-E, thus providing a new opportunity for the development of anticancer agents targeting kinesins.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Fluoroindoline, is researched, Molecular C8H8FN, CAS is 2343-22-8, about Rh(III)-Catalyzed direct C-7 amination of indolines with anthranils, the main research direction is pyrimidylindoline anthranil preparation rhodium catalyst amination; pyrimidylindolinyl aminobenzaldehyde preparation.Quality Control of 5-Fluoroindoline.

An efficient and practical method for the C-7 amination of indolines via Rh(III)-catalyzed C-H activation was reported. This reaction afforded various C-7 aminated indolines in good to excellent yields by using readily available anthranils as the aminating agents. The corresponding indolines with an amino and a carbonyl group together provided an opportunity for the construction and modification of diverse indoles and indolines in the pharmaceutical industry.

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Computed Properties of C8H8FN. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Fluoroindoline, is researched, Molecular C8H8FN, CAS is 2343-22-8, about Design, synthesis and biological evaluation of novel 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole triazole derivatives as potent TRPV1 antagonists. Author is Li, Jinyu; Nie, Cunbin; Qiao, Yue; Hu, Jing; Li, Qifei; Wang, Qiang; Pu, Xiaohui; Yan, Lin; Qian, Hai.

The design, synthesis, and pharmacol. evaluation of a class of TRPV1 antagonists constructed on 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole as A-region and triazole as B-region I (R = 2-Cl 2,5-Me2, 2-NO2-4-Cl, etc.) have been reported. The SAR anal. indicated that 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole analogs I displayed excellent antagonism of hTRPV1 activation by capsaicin and showed better potency compared to the corresponding dihydroindole analogs. Optimization of this design led to the eventual identification of compound I (R = 2-CF3), a potent TRPV1 antagonist. In vitro, using cells expressing recombinant human TRPV1 channels, I (R = 2-CF3) displayed potent antagonism activated by capsaicin (IC 50 = 0.075 μM) and only partially blocked acid activation of TRPV1. In vivo, I (R = 2-CF3) exhibited good efficacy in capsaicin-induced and heat-induced pain models and had almost no hyperthermia side-effect. Furthermore, pharmacokinetic studies revealed that compound I (R = 2-CF3) had a superior oral exposure after oral administration in rats. To understand its binding interactions with the receptor, the docking study of I (R = 2-CF3) was performed in rTRPV1 model and showed an excellent fit to the binding site. On the basis of its superior profiles, I (R = 2-CF3) could be considered as the lead candidate for the further development of antinociceptive drugs.

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Formula: C8H8FN. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-Fluoroindoline, is researched, Molecular C8H8FN, CAS is 2343-22-8, about Oxidative Palladium(II)-Catalyzed C-7 Alkenylation of Indolines. Author is Jiao, Lin-Yu; Oestreich, Martin.

N-(dimethylcarbamoyl)indolines such as I underwent regioselective and stereoselective alkenylation with electron-deficient alkenes and styrenes RR1C:CHR2 [R = BuO2C, MeO2C, EtO2C, PhCH2O2C, MeCO, NC, (EtO)2P(:O), Ph, F5C6, 4-FC6H4, 4-ClC6H4, 2-ClC6H4, 2-BrC6H4; R1, R2 = H, Me] with 1,4-benzoquinone in acetic acid in the presence of Pd(OAc)2 and p-toluenesulfonic acid to give (E)-7-alkenylindolinecarboxamides such as II in 21-89% yield and all except II (R = MeO2C; R1 = H; R2 = Me) as the (E)-isomers in >98:2 dr. The tetrasubstituted urea moiety functioned as a directing group for directed alkenylation; non-urea directing groups either yielded alkenylation products in low (20%) yield or did not yield alkenylation products. An ethylcarbamoylindoline underwent alkenylation with Bu acrylate followed by cyclization to give oxoindolopyrimidineacetate III.

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Formula: C8H8FN. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Fluoroindoline, is researched, Molecular C8H8FN, CAS is 2343-22-8, about Palladium-Catalyzed Remote 1,n-Arylamination of Unactivated Terminal Alkenes. Author is Han, Chunhua; Fu, Zhiyuan; Guo, Songjin; Fang, Xinxin; Lin, Aijun; Yao, Hequan.

A palladium-catalyzed remote 1,n-arylamination (from 1,3- to 1,11-arylamination) of unactivated terminal alkenes with aryl iodides and arylamines has been realized. This three-component reaction proceeded via Pd-catalyzed Heck arylation, alkene isomerization, and aza-Michael addition, exhibiting good regio- and chemoselectivity, and wide substrate scope. Preliminary mechanistic studies indicated that the in situ generated ortho/para-quinone methide intermediates served as the driving force for the alkene isomerization and promoted the rearomatization upon nucleophilic amination.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Fluoroindoline( cas:2343-22-8 ) is researched.Quality Control of 5-Fluoroindoline.Pang, Shaofeng; Liu, Fangfang; Zhang, Yujing; Dong, Zhaowen; Su, Qiong; Wang, Wenfang; Li, Zhenhua; Zhou, Feng; Wang, Yanbin published the article 《Construction of Functional Superhydrophobic Biochars as Hydrogen Transfer Catalysts for Dehydrogenation of N-Heterocycles》 about this compound( cas:2343-22-8 ) in ACS Sustainable Chemistry & Engineering. Keywords: construction functional superhydrophobic biochars hydrogen transfer catalyst dehydrogenation nitrogen. Let’s learn more about this compound (cas:2343-22-8).

To endow metal-free materials with the high catalytic activity that is typically featured by a metal-based catalyst is yet a constant pursuit in the field of catalytic chem. In this work, novel functional biochars (DCNs) were prepared from wheat straw for the first time via a simple strategy of reconstructing the catalytic active sites in carbon precursors and subsequent controlled carbonization, which may be further applied in the oxidative dehydrogenation of N-heterocycles with ambient air as the oxidant. Whereas the superhydrophobicity of DCN-850 can effectively remove the only byproduct water to effectively reduce the possible effects of water on the catalyst, it also can decrease mass transfer resistance on active sites, thereby ensuring the reaction with high efficiencies and good generality. Especially, after several reuses, the activity and structures of DCN-850 remained unchanged in the catalytic system with water as a solvent. Furthermore, various characterization technologies and the model reaction were used to investigate the architectural attributes of DCNs, and the results show that there is a pos. correlation between the catalytic performance and hydrophobicity of DCNs, as well as reveal that the catalytic active sites may be made up of a five-membered-ring ketone or its enol form and possibly a phenolic unit, which could be encapsulated in internal structures of catalysts and promote the reaction via the recycling of -C-C-OH and -C-C=O groups by the pathway of catalytic hydrogen transfer.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Fluoroindoline, is researched, Molecular C8H8FN, CAS is 2343-22-8, about Rh(III)-Catalyzed direct C-7 amination of indolines with anthranils, the main research direction is pyrimidylindoline anthranil preparation rhodium catalyst amination; pyrimidylindolinyl aminobenzaldehyde preparation.Quality Control of 5-Fluoroindoline.

An efficient and practical method for the C-7 amination of indolines via Rh(III)-catalyzed C-H activation was reported. This reaction afforded various C-7 aminated indolines in good to excellent yields by using readily available anthranils as the aminating agents. The corresponding indolines with an amino and a carbonyl group together provided an opportunity for the construction and modification of diverse indoles and indolines in the pharmaceutical industry.

Here is just a brief introduction to this compound(2343-22-8)Quality Control of 5-Fluoroindoline, more information about the compound(5-Fluoroindoline) is in the article, you can click the link below.

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Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics