Category: 20028-53-9

Gisbert, Patricia; Albert-Soriano, Maria; Pastor, Isidro M. published the article 《Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C-C and C-N Bond Formation》. Keywords: aminobenzaldehyde ketone biscarboxymethyl imidazolium chloride catalyst green tandem cyclization; quinoline preparation; aminoaryl ketone biscarboxymethyl imidazolium chloride catalyst green tandem cyclization; acridine preparation.They researched the compound: 2-Amino-5-chlorobenzaldehyde( cas:20028-53-9 ).Computed Properties of C7H6ClNO. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:20028-53-9) here.

Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2-aminobenzaldehydes and 2-aminoaryl ketones under solvent-free conditions, employing 1,3-bis(carboxymethyl)-imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Addnl., 3-acetylquinolines have been transformed, under solvent-free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E-factors are in the range of 14-23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Amino-5-chlorobenzaldehyde(SMILESS: NC1=CC=C(Cl)C=C1C=O,cas:20028-53-9) is researched.Electric Literature of C7H6ClNO. The article 《Highly Regioselective Friedlaender Annulations with Unmodified Ketones Employing Novel Amine Catalysts: Syntheses of 2-Substituted Quinolines, 1,8-Naphthyridines, and Related Heterocycles》 in relation to this compound, is published in Journal of Organic Chemistry. Let’s take a look at the latest research on this compound (cas:20028-53-9).

Catalysts were evaluated on the preparation of 2-substituted quinolines, 1,8-naphthyridines, and chromone derivatives, e.g., I-III, resp., from unmodified Me ketones and o-aminoarom. aldehydes. While oxide catalysts yielded the 2,3-dialkyl substituted products, cyclic secondary amines provided the 2-alkylsubstituted products regioselectively. In particular, pyrrolidine derivatives provided the highest regioselectivity favoring the 2-substituted products. The most reactive and regioselective catalyst was the bicyclic pyrrolidine derivative, TABO (1,3,3-trimethyl-6-azabicyclo[3.2.1]octane), yielding 1,8-naphthyridines with as high as 96:4 regioselectivity. Regioselectivity increased with slow addition of the Me ketone substrate to the reaction mixture, and was pos. related to temperature Isolated yields of single regioisomers were typically 65-84%, while observed regioselectivities were ≥90:10 for 1,8-naphthyridines and ≥84:16 for quinolines.

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Ren, Lei; Lei, Tao; Ye, Jia-Xi; Gong, Liu-Zhu researched the compound: 2-Amino-5-chlorobenzaldehyde( cas:20028-53-9 ).Electric Literature of C7H6ClNO.They published the article 《Step-Economical Synthesis of Tetrahydroquinolines by Asymmetric Relay Catalytic Friedlaender Condensation/Transfer Hydrogenation》 about this compound( cas:20028-53-9 ) in Angewandte Chemie, International Edition. Keywords: diastereoselective enantioselective synthesis hydroquinoline catalytic Friedlander condensation transfer hydrogenation; chiral Bronsted achiral Lewis acid catalyst stereoselective synthesis hydroquinoline. We’ll tell you more about this compound (cas:20028-53-9).

The title relay reaction relies on a combination of an achiral Lewis acid and a chiral Bronsted acid (BINOL phosphoric acid diester). This one-pot method provides access to tetrahydroquinoline derivatives with multiple contiguous stereocenters in high stereoselectivity (>20:1 dr, 98% ee).

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called A Facile Synthesis of 2-Methylquinolines via Pd-Catalyzed Aza-Wacker Oxidative Cyclization, published in 2008-01-17, which mentions a compound: 20028-53-9, Name is 2-Amino-5-chlorobenzaldehyde, Molecular C7H6ClNO, Related Products of 20028-53-9.

A novel Pd-catalyzed Wacker-type oxidative cyclization under air is described. By using this cyclization, a series of 2-methylquinolines, e.g., I, are readily prepared with good yields under mild conditions.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called N-Heterocyclic carbene copper catalyzed quinoline synthesis from 2-aminobenzyl alcohols and ketones using DMSO as an oxidant at room temperature, published in 2019, which mentions a compound: 20028-53-9, Name is 2-Amino-5-chlorobenzaldehyde, Molecular C7H6ClNO, HPLC of Formula: 20028-53-9.

A facile and practical process for the synthesis of quinolines through an N-heterocyclic carbene copper catalyzed indirect Friedlander reaction from 2-aminobenzyl alc. and aryl ketones using DMSO as an oxidant at room temperature is reported. The quinolines, e.g., I (R1 = 4-MeC6H4, 2-ClC6H4, 3-thienyl, etc., R2 = H; R1 = Ph, R2 = Me), were synthesized in acceptable yields.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Name: 2-Amino-5-chlorobenzaldehyde. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Eco-Friendly Catalytic Systems Based on Carbon-Supported Magnesium Oxide Materials for the Friedlaender Condensation. Author is Godino-Ojer, Marina; Lopez-Peinado, Antonio J.; Martin-Aranda, Rosa M.; Przepiorski, Jacek; Perez-Mayoral, Elena; Soriano, Elena.

Carbon-supported MgO materials are excellent and sustainable catalysts for the synthesis of N-containing heterocyclic compounds by the Friedlaender condensation under mild, solvent-free conditions. The results reported herein indicate that MgO is the most active catalytic species that accelerates the reaction compared with the catalytic behavior observed for the carbon material Norit RX3. On the basis of DFT calculations, a reaction mechanism that involves dual activation of the reacting structures by the catalyst is proposed.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Synthesis and Pharmacological Evaluation of Tetrahydro-γ-carboline Derivatives as Potent Anti-inflammatory Agents Targeting Cyclic GMP-AMP Synthase.Reference of 2-Amino-5-chlorobenzaldehyde.

The activation of cyclic GMP-AMP synthase (cGAS) by double-stranded DNA is implicated in the pathogenesis of many hyper inflammatory and autoimmune diseases, and the cGAS-targeting small mol. has emerged as a novel therapeutic strategy for treating these diseases. However, the currently reported cGAS inhibitors are far beyond maturity, barely demonstrating in vivo efficacy. Inspired by the structural novelty of compound I (G140), a structural optimization on both its side chain and the central tricyclic core, leads to several subseries of compounds, including those unexpectedly cyclized complex ones. Compound II (R = aminomethyl) bearing an N-glycylglycinoyl side chain was identified as the most potent one with cellular IC50 values of 1.38 and 11.4μM for h- and m-cGAS, resp. Mechanistic studies confirmed its direct targeting of cGAS. Further, compound II (R = aminomethyl) showed superior in vivo anti-inflammatory effects in the lipopolysaccharide-induced mouse model. The encouraging result of compound II (R = aminomethyl) provides solid evidence for further pursuit of cGAS-targeting inhibitors as a new anti-inflammatory treatment.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Computed Properties of C7H6ClNO. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Cobalt oxide-carbon nanocatalysts with highly enhanced catalytic performance for the green synthesis of nitrogen heterocycles through the Friedlander condensation. Author is Godino-Ojer, Marina; Lopez-Peinado, Antonio J.; Maldonado-Hodar, Francisco J.; Bailon-Garcia, Esther; Perez-Mayoral, Elena.

A novel series of eco-sustainable catalysts developed by supporting CoO nanoparticles on different carbon supports, highly efficient in the synthesis of quinolines and naphthyridines, through the Friedlander condensation, are reported for the first time. Textural properties, dispersion and location of the Co-phase are influenced by the nature of the carbon support, Co-precursor salt and metal loading, having a significant impact on the catalytic performance. Thus, the presence of the mesopores and macropores in carbon aerogels together with the homogeneous distribution of the active phase favors the formation of product 3a as a function of the metal loading. However, an increase in the metal content when using CNTs indicates the formation of CoO aggregates and an optimal concentration of 3 wt% CoO was observed, providing the highest conversion values. The carbon-based catalysts herein reported can be considered to be a sustainable alternative having advantages such as easy preparation, superior stability and notably enhanced catalytic performance, operating at lower temperature and under solvent-free conditions.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

SDS of cas: 20028-53-9. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Synthesis of quinolines and naphthyridines via catalytic retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes or nicotinaldehydes. Author is Zhang, Song-Lin; Deng, Zhu-Qin.

A Cu(I)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Synthetic Route of C7H6ClNO. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Friedlander synthesis and structure characterization of novel quinoline derivatives.

A series of 2-fluoro-6H-chromeno[4,3-b]quinoline derivatives I (R = H, 5-Cl, 3,5-Br2, 3,6-(MeO)2) were synthesized by the Friedlander condensation of substituted (unsubstituted) o-aminobenzaldehyde with 6-fluorochroman-4-one in alk. ethanol solutions In addition, the expected products can give 2-(3-(ethoxymethyl)quinolin-2-yl)-4-fluorophenol derivatives II (R = H, 5-Cl, 3,5-Br2, 3,6-(MeO)2) by nucleophilic substitution reaction in alk. solutions The structures of the title compounds I and II were characterized by elemental anal., IR, 1H NMR and MS techniques. The compound II(R = 3,6-(MeO)2) was confirmed by X-ray single crystal diffraction anal.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem