Chiral nitrogen ligands

Category: chiral-nitrogen-ligands. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Tri(naphthalen-1-yl)phosphine, is researched, Molecular C30H21P, CAS is 3411-48-1, about Palladium-Catalyzed Coupling of Optically Active Amines with Aryl Bromides. Author is Wagaw, Seble; Rennels, Roger A.; Buchwald, Stephen L..

The coupling of enantiomerically enriched amines with aryl bromides produces the corresponding N-aryl derivatives The choice of ligand in the palladium-catalyzed coupling is critical to the formation of the anilines without loss of enantiomeric purity. While LnPd [L = P(o-tolyl)3] successfully catalyzes the intramol. aryl amination of α-substituted optically pure amines, intermol. coupling reactions with this catalyst system gives racemized products. In contrast, intermol. N-arylations employing LnPd [L = (±)-BINAP] gives products in good yields with no erosion of enantiopurity. A mechanism for the observed racemization is proposed. The utility of the intramol. process is demonstrated by the synthesis of 3, an intermediate in the formal synthesis of 4, a potent ACE inhibitor.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1,5-Dibromopentane( cas:111-24-0 ) is researched.Category: chiral-nitrogen-ligands.Shan, Naisong; Shen, Chengtian; Evans, Christopher M. published the article 《Critical Role of Ion Exchange Conditions on the Properties of Network Ionic Polymers》 about this compound( cas:111-24-0 ) in ACS Macro Letters. Keywords: ion exchange network ionic polymer. Let’s learn more about this compound (cas:111-24-0).

Ionic polymers are important in a wide range of applications and can exhibit widely different properties depending on the ionic species. In the case of single ion conducting polymers, where one charge is attached to the backbone or as a side group, ion exchange is performed to control the mobile species. While the conditions are often specified, the final ion content is not always quantified and there are no clear criteria for what concentration of salt is needed in the exchange. A series of ammonium network ionic polymers with different precise carbon spacers (C4-C7) between ionic junctions was synthesized as a model system to understand how ion exchange conditions impact the resultant polymer properties. The initial networks with free bromide anions were exchanged with 1.5, 3, or 10 equiv of lithium bis(trifluoromethane) sulfonimide (LiTFSI) salt in solution For networks with seven carbons between crosslinks, increasing the LiTFSI concentration lead to an increase in ion exchange efficiency from 83.7 to 97.6 mol %. At the highest conversion, the C7 network shows a 4°C decrease in glass transition temperature, 50°C increase in degradation temperature, 12-fold lower water uptake from air, and greater than 10-fold increase in conductivity at 90°C. These results illustrate that properties such as Tg are less sensitive to residual ion impurities, while conductivity is highly dependent on the final exchange conversion.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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.Al-Janabi, Emaad M. A.; Hatshan, Mohammad R.; Adil, Syed Farooq; Kadhum, Wesam R.; Al-Jibori, Subhi A.; Faihan, Ahmed S.; Al-Janabi, Ahmed S. researched the compound: 1,2-Bis(diphenylphosphino)ethane( cas:1663-45-2 ).Synthetic Route of C26H24P2.They published the article 《Spectroscopic, antibacterial and anti-cancer studies of new platinum(II)-diethyldithiocarbamate mixed ligand complexes with phosphine or amine ligands》 about this compound( cas:1663-45-2 ) in Journal of Molecular Structure. Keywords: platinum diethyldithiocarbamate phosphine amine complex preparation antibacterial antitumor activity. We’ll tell you more about this compound (cas:1663-45-2).

A series of new platinum(II) mixed ligand complexes of diethyldithiocarbamate (Et2DT) and phosphine or amine ligands of the type [Pt(Et2DT)2(diphosphine)] (3-6), [Pt(Et2DT)2(diamine)](7-8), [Pt(Et2DT)2(PPh3)2] (9) and [Pt(Et2DT)2(SPPh3)2](10) have been prepared in good yield and fully characterized by elemental anal., conductivity measurements and spectroscopic data (i.r., 1H, 31P-{1H} nmr). Our interest in these types of complexes are based on the fact that these complexes are known for their promising biol. activity, and could possess interesting coordination modes, which are poorly represented in the literature. Therefore, the prepared complexes were tested for their anti-bacterial against three types of pathogenic bacteria namely S. aureus, E. coli, and p. aeruginosa. In addition, four of the prepared complexes were screened for their anti-cancer activity against lung cancer cell lines, and that the [Pt(Et2DT)2(bipy)] was significantly more potent with IC50 value is 1.0 ± 0.2μM, but the [Pt(Et2DT)2(dppf)] was practically inactive in the selected dose range with IC50 value is 32.0 ± 3.0μM.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1,5-Dibromopentane( cas:111-24-0 ) is researched.Reference of 1,5-Dibromopentane.Qiu, Shaotong; Gao, Xiang; Zhu, Shifa published the article 《Dirhodium(II)-catalysed cycloisomerization of azaenyne: rapid assembly of centrally and axially chiral isoindazole frameworks》 about this compound( cas:111-24-0 ) in Chemical Science. Keywords: aromatic azaenyne dirhodium catalyst diastereoselective enantioselective regioselective cycloisomerization; aryl isoindazole preparation. Let’s learn more about this compound (cas:111-24-0).

A dirhodium(II)-catalyzed asym. cycloisomerization reaction of azaenynes through a cap-tether synergistic modulation strategy, which represents the first catalytic asym. cycloisomerization of azaenynes. This reaction is highly challenging because of its inherent strong background reaction leading to racemate formation and the high capability of coordination of the nitrogen atom resulting in catalyst deactivation. Varieties of centrally chiral isoindazole derivatives was prepared in up to 99 : 1 d.r., 99 : 1 er and 99% yield and diverse enantiomerically enriched atropisomers bearing two five-membered heteroaryls was accessed by using an oxidative central-to-axial chirality transfer strategy. The tethered nitrogen atom incorporated into the starting materials enabled easy late-modifications of the centrally and axially chiral products via C-H functionalizations, which further demonstrated the appealing synthetic utilities of this powerful asym. cyclization.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Preparation and aminolysis of 4-hydroxyquinazoline-2-sulfonic acid, published in 1965, which mentions a compound: 20198-19-0, mainly applied to , Category: chiral-nitrogen-ligands.

A saturated solution of KMnO4 is added to a solution of 8.9 g. 2-mercapto-4-hydroxyquinazoline (I) and 28 g. KOH in 100 ml. H2O at 45°, the mixture filtered, and the filtrate cooled to 0°. AcOH is added to a pH 6.5, the whole cooled to -5°, and the precipitate filtered off, and recrystallized from 70% EtOH at 0° to give a 60% yield of K 4-hydroxyquinazoline-2-sulfonate (II) (no m.p.). II is adjusted with HCl to pH 4 and heated to 100° to yield 2,4-dihydroxyquinazoline, m. 348-50°. II (2.64 g.) in 6 ml. of 2M aqueous Me2NH heated 4 hrs. at 130° gives 1.74 g. of 2-dimethylamino-4-hydroxyquinazoline (III), m. 244-6°. III.HCl m. 275°. The following analogs (IV) of III were prepared (R, % yield, m.p., and m.p. Ac derivative given): H, 90.6, 315-16°, 278-80°; Me, 74.2, 275-6°, 194-6°; Et, 82.9, 231-2°, 120-2°; Pr, 84.5, 199-200°, 118-19°; Bu, 88.4, 187-8°, 110-12°; Ph, 89.7, 260-3°, 203-4°; CH2Ph, 92.2, 214-15°, 124-5°; C6H4OMe-p, 85.7, 271-2°, 204-5°; C6H4Me-p, 91.2, 268-70°, 206-9°; cyclohexyl, 32.0, 209-11°, 204-5°; CH2CH2OH, 96.0,249-50°, -; 1-pyrrolidyl 73.2, 223-4°, -.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 3411-48-1, is researched, Molecular C30H21P, about Structural and photophysical characterization of gold(I) complexes bearing naphthyl chromophores, the main research direction is gold chloro complex naphthylphosphine naphthyl isonitrile preparation crystal structure; fluorescence gold chloro complex naphthylphosphine naphthyl isonitrile; phosphorescence gold chloro complex naphthylphosphine naphthyl isonitrile.HPLC of Formula: 3411-48-1.

The authors prepared two chlorido-Au(I) complexes L-Au-Cl bearing a naphthyl moiety. Complex 1 with L = tris(1-naphthyl)phosphine shows standard linear coordination without further aggregation in the solid state. Complex 2 with L = 2-naphthyl isonitrile is engaged in a complex network of aurophilic and π-π interactions. The two complexes show similar luminescence behavior in solution at room temperature with both intraligand fluorescence and phosphorescence. At 77 K the emission spectra are dominated by intraligand phosphorescence, which is typical of Au complexes with extended π-chromophores.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

SDS of cas: 1663-45-2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 1,2-Bis(diphenylphosphino)ethane, is researched, Molecular C26H24P2, CAS is 1663-45-2, about Carboxylation of a Palladacycle Formed via C(sp3)-H Activation: Theory-Driven Reaction Design. Author is Kanna, Wataru; Harabuchi, Yu; Takano, Hideaki; Hayashi, Hiroki; Maeda, Satoshi; Mita, Tsuyoshi.

Theory-driven organic synthesis is a powerful tool for developing new organic transformations. A palladacycle(II), generated from 8-methylquinoline via C(sp3)-H activation, is frequently featured in the scientific literature, albeit that the reactivity toward CO2, an abundant, inexpensive, and non-toxic chem., remains elusive. Authors have theor. discovered potential carboxylation pathways using the artificial force induced reaction (AFIR) method, a d.-functional-theory (DFT)-based automated reaction path search method. The thus obtained results suggest that the reduction of Pd(II) to Pd(I) is key to promote the insertion of CO2. Based on these computational findings, they employed various one-electron reductants, such as Cp*2Co, a photoredox catalyst under blue LED irradiation, and reductive electrolysis ((+)Mg/(-)Pt), which afforded the desired carboxylated products in high yields. After screening phosphine ligands under photoredox conditions, they discovered that bidentate ligands such as dppe promoted this carboxylation efficiently, which was rationally interpreted in terms of the redox potential of the Pd(II)-dppe complex as well as on the grounds of DFT calculations They are convinced that these results could serve as future guidelines for the development of Pd(II)-catalyzed C(sp3)-H carboxylation reactions with CO2.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Fernandes, Daniel J.; Cardenas, Rafael M.; Bertino, Joseph R.; Hynes, John B. published an article about the compound: 2-Aminoquinazolin-4(3H)-one( cas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2 ).Formula: C8H7N3O. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:20198-19-0) through the article.

A series of title compounds (I; Z = NHCH2, CH2NH, CH2NMe, CH2S, CH2O, (CH2)2, CHONCH2) were evaluated as inhibitors of colon adenocarcinoma and the folate-dependent enzymes, thymidylate synthase  [9031-61-2] and dihydrofolate reductase  [9002-03-3]. Of the drugs tested, IAHQ (I; Z = NHCH2) [56239-21-5], when administered at 85 mg/kg on days 2 and 10 after tumor implantation, delayed the growth of colon tumor Number 38, and resulted in 6 of 20 tumor-free animals at 90 days. In contrast, methotrexate had no effect on the growth of colon tumor Number 38 at maximally tolerated doses. IAHQ was also active against human colon adenocarcinoma cells (HCT-8) in tissue culture, requiring a concentration of 5 × 10-7 M to inhibit cell growth by 50% after 72 h continuous exposure.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-(4-Pyridyl)-1H-tetrazole(SMILESS: C1(C2=NN=NN2)=CC=NC=C1,cas:14389-12-9) is researched.Safety of 2-(7-Bromo-1H-indol-3-yl)acetic acid. The article 《Secondary spacer modulated assembly of polyoxometalate based metal-organic frameworks》 in relation to this compound, is published in Dalton Transactions. Let’s take a look at the latest research on this compound (cas:14389-12-9).

To study the influence of a secondary spacer on the resulting structures of POMOFs containing pytz, five new compounds with different dimensionalities, [Cu5(2-pytz)6(H2O)4][SiMo12O40]·3H2O (1), [Cu3(2-pytz)4bipy][H2SiMo12O40]·bipy (2), [Cu3(2-pytz)2(bipy)4(H2O)6][H4SiW12O40]2·6H2O (3), [Cu2(2-pytz)(phen)(OH)]2[SiW12O40]·H2O (4), [Cu3(4-pytz)4(H2O)4][H2SiW12O40]·2H2O (5) (pytz = pyridyltetrazole), were synthesized. When only 2-pytz was employed, compound 1 with a 3D framework was obtained, whereas when the secondary spacers (4,4′-bipy, phen and 4-pytz) were introduced into the reaction system of 1, compounds 2-5 were obtained and exhibit a broad range of structures, including 0D, 1D, 2D and 3D frameworks. It can be observed from the architectures of compounds 1-5 that the secondary spacers have a great effect on the structures of the MOFs, which gave various dimensional POMOF compounds Addnl., photocatalytic experiments of 1-5 for the photocatalytic degradation of RhB under UV irradiation were also studied.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Acta Crystallographica, Section E: Crystallographic Communications called Crystal structure of 1-[(6-chloropyridin-3-yl)sulfonyl]-1,2,3,4-tetrahydroquinoline, Author is Jeyaseelan, S.; Rajegowda, H. R.; Britto Dominic Rayan, R.; Raghavendra Kumar, P.; Palakshamurthy, B. S., which mentions a compound: 6684-39-5, SMILESS is ClC1=NC=C(C=C1)[S](=O)(=O)Cl, Molecular C5H3Cl2NO2S, HPLC of Formula: 6684-39-5.

The tetrahydropyridine ring of the quinoline system in the title compound, C14H13ClN2O2S, adopts a half-chair conformation with the bond-angle sum at the N atom being 350.0°. The dihedral angle between the least-squares planes of the two aromatic rings is 50.13 (11)°. In the crystal, inversion dimers linked by pairs of C-H···O hydrogen bonds generate R 2 2(10) loops. Addnl. intermol. C-H···O hydrogen bonds generate C(7) chains along [100].

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis