Chiral nitrogen ligands

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Triarylpyridylmethanes》. Authors are Adams, Roger; Hine, Jack; Campbell, John.The article about the compound:2-Chloro-5-pyridinesulfonyl chloridecas:6684-39-5,SMILESS:ClC1=NC=C(C=C1)[S](=O)(=O)Cl).Related Products of 6684-39-5. Through the article, more information about this compound (cas:6684-39-5) is conveyed.

The Na salt of 2-hydroxypyridine (I) and p-O2NC6H4SO2Cl give 80% 2-pyridyl p-nitrobenzenesulfonate, m. 157-60° (m.ps. corrected). 2-Pyridyl benzoate (11.1 g.) and 27 g. AlCl3, heated 3 hrs. at 180°, give 0.8% 5-benzoyl-2-hydroxypyridine, m. 194-6°; this was prepared in 66% yield from 2-hydroxy-5-pyridinecarboxylic acid through the acid chloride. 1-Methyl-2-pyridone-5-sulfonic acid (13.5 g.) and 26 g. PCl5, heated 2 hrs. at 125°, give 76% of the acid chloride, m. 50-1°; amide (II) m. 157-9°. 2-Chloro-N-2-pyridyl-5-pyridinesulfonamide, prepared in 66% yield from 2-chloro-5-pyridinesulfonyl chloride and 2-aminopyridine in C6H6, m. 237-9°. II and MeONa in MeOH, refluxed 60 hrs., give 77% 2-methoxy-5-pyridinesulfonamide, m. 149-50°. The melt of I (3 g.) and 3 g. Ph3COH, treated with 2 drops concentrated H2SO4 and heated 20 min. at 250°, gives 48% 5-(triphenylmethyl)-2-hydroxypyridine (IV), m. 365-8°; 3-Me derivative m. 260-2°, 54%; the 5-[(4-biphenylyl)diphenylmethyl] analog of IV m. 298-300°, 58%; its 3-Me derivative m. 307-10°, 56%. The same compounds result from Ph3CCl without catalyst. 6-Methyl-2-hydroxypyridine and Ph3COH give 22% (Ph3CCl gives 9%) 3-(triphenylmethyl)-6-methyl-2-hydroxypyridine, m. 314-17°, which does not react with POCl3. IV and a 6-fold excess of POCl3, heated 48 hrs. on the steam bath (sealed tube), give 48% of the 2-chloro analog (V), m. 256-7°; 3-Me derivative m. 130° and then 151-2°, 92%; the 5-[(4-biphenylyl)diphenylmethyl] analog of V m. 182-3°, 95%; its 3-Me derivative m. 158-9°, 93%. V in absolute EtOH, reduced 6 hrs. over Raney Ni at 70°/45 lb., gives 66% 3-(triphenylmethyl)pyridine (VI), m. 269-70°; 5-Me derivative m. 153-4°, 83%; the 3-[(4-biphenylyl)diphenylmethyl] analog of VI m. 195-6°, 91%; its 5-Me derivative m. 188-9°, 91%. VI exhibits a marked phosphorescence after irradiation with ultraviolet light at room temperature; the greenish white afterglow lasts only 1 sec. The infrared absorption spectra of VI and CPh4 are similar. IV (0.8 g.), 0.67 g. ClCH2CO2H, and 0.85 g. KOH in 25 ml. absolute EtOH, refluxed 6 hrs., give 92% 1-(carboxymethyl)-5-(triphenylmethyl)-2(1H)-pyridone, m. 264-6°.

From this literature《Triarylpyridylmethanes》,we know some information about this compound(6684-39-5)Related Products of 6684-39-5, but this is not all information, there are many literatures related to this compound(6684-39-5).

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

COA of Formula: C8H7N3O. 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: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Exploration of a New Type of Antimalarial Compounds Based on Febrifugine. Author is Kikuchi, Haruhisa; Yamamoto, Keisuke; Horoiwa, Seiko; Hirai, Shingo; Kasahara, Ryota; Hariguchi, Norimitsu; Matsumoto, Makoto; Oshima, Yoshiteru.

Febrifugine (I), a quinazoline alkaloid, isolated from Dichroa febrifuga roots, shows powerful antimalarial activity against Plasmodium falciparum. The use of I as an antimalarial drug has been precluded because of side effects, such as diarrhea, vomiting, and liver toxicity. However, the potent antimalarial activity of I has stimulated medicinal chemists to pursue compounds derived from I, which may be valuable leads for novel drugs. In this study, we synthesized a new series of febrifugine derivatives formed by structural modifications at (i) the quinazoline ring, (ii) the linker, or (iii) the piperidine ring. Then, we evaluated their antimalarial activities. Thienopyrimidine analog II exhibited a potent antimalarial activity and a high therapeutic selectivity both in vitro and in vivo, suggesting that II is a good antimalarial candidate.

There is still a lot of research devoted to this compound(SMILES：O=C1NC(N)=NC2=C1C=CC=C2)COA of Formula: C8H7N3O, and with the development of science, more effects of this compound(20198-19-0) can be discovered.

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

Reference of Tri(naphthalen-1-yl)phosphine. 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: Tri(naphthalen-1-yl)phosphine, is researched, Molecular C30H21P, CAS is 3411-48-1, about Palladium-Catalyzed Cross-Coupling of N-Sulfonylaziridines with Boronic Acids. Author is Duda, Megan L.; Michael, Forrest E..

A mild palladium-catalyzed cross-coupling of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is presented. The reaction is highly regioselective and compatible with diverse functionality. A catalytic amount of base, a sterically demanding triarylphosphine ligand, and a phenol additive are critical to the success of the reaction. Coupling of a deuterium-labeled substrate established that ring opening of the aziridine occurs with inversion of stereochem.

There is still a lot of research devoted to this compound(SMILES：C1=CC2=C(C=C1)C(=CC=C2)P(C1=CC=CC2=C1C=CC=C2)C1=CC=CC2=C1C=CC=C2)Reference of Tri(naphthalen-1-yl)phosphine, and with the development of science, more effects of this compound(3411-48-1) can be discovered.

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

Name: 5-(4-Pyridyl)-1H-tetrazole. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about In-situ hydrothermal preparation of a novel 3D CuI-based tetrazole coordination polymer with pseudo-porphyrin secondary building units. Author is Dong, Dapeng; Yu, Naisen; Cong, Yan; Zhao, Ying; Zhao, Haiyan; Liu, Dedi; Li, Zhenghua; Liu, Jia; Liu, Dongping.

A novel 3-dimensional CuI-based tetrazole coordination polymer through the employment of in-situ solvothermal techniques by using 4-cyanopyridine, NaN3 and CuI, [Cu5(L)3I2] (1) (HL = 5-(4-pyridyl)-1H-tetrazole) was synthesized and structurally characterized by x-ray single-crystal diffraction as well as by powder X-ray diffraction, elemental anal. and TGA. In compound 1, each CuN3I tetrahedron, CuN2I2 tetrahedron and CuN3 triangle are linked to each other by L ligand to form a 3-dimensional framework structure. It is interesting to note that the interconnection of Cu1 and Cu2 ions by bridging L ligand form pseudo-porphyrin secondary building units. Surface photovoltage, field-induced surface photovoltage and luminescent properties of compound 1 also were studied.

There is still a lot of research devoted to this compound(SMILES：C1(C2=NN=NN2)=CC=NC=C1)Name: 5-(4-Pyridyl)-1H-tetrazole, and with the development of science, more effects of this compound(14389-12-9) can be discovered.

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

Name: 2-Aminoquinazolin-4(3H)-one. 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: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Dicopper complexes catalyzed coupling/cyclization of 2-bromobenzoic acids with amidines leading to quinazolinones. Author is Hung, Ming-Uei; Liao, Bei-Sih; Liu, Yi-Hong; Peng, Shie-Ming; Liu, Shiuh-Tzung.

Dicopper(I) complexes {[Cu2(bpnp)(MeCN)4](PF6)2} (I), {[Cu2(bpnp)(MeCN)4](BAr4F)2} {BAr4F = B[C6H3-3,5-(CF3)2]4}, and [Cu2(bpnp)Cl2] (II) were prepared from the complexation of [Cu(MeCN)4](PF6) with 2,7-bis(2-pyridyl)-1,8-naphthyridine (bpnp) followed by anion metathesis and treatment of chloride sequentially. X-ray structural anal. of II (data deposited with the CCDC) indicates the mol. to have a 2-fold axis passing through the Cu2Cl2 core, which has the shape of a butterfly, and that the Cu atom is tetrahedrally coordinated with in a Cl2N2 donor set. In preliminary experiments, I was found to be an effective catalyst in the coupling/cyclization of 2-bromobenzoic acids with amidines, providing the corresponding quinazolinones in good yields. Copyright © 2014 John Wiley & Sons, Ltd.

There is still a lot of research devoted to this compound(SMILES：O=C1NC(N)=NC2=C1C=CC=C2)Name: 2-Aminoquinazolin-4(3H)-one, and with the development of science, more effects of this compound(20198-19-0) can be discovered.

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 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 Functionalizing Polystyrene with N-Alicyclic Piperidine-Based Cations via Friedel-Crafts Alkylation for Highly Alkali-Stable Anion-Exchange Membranes, published in 2020-06-23, which mentions a compound: 111-24-0, Name is 1,5-Dibromopentane, Molecular C5H10Br2, SDS of cas: 111-24-0.

Different anion-exchange membranes (AEMs) based on polystyrene (PS)-carrying benzyltrimethyl ammonium cations are currently being developed for use in alk. fuel cells and water electrolyzers. However, the stability in relation to these state-of-the-art cations needs to be further improved. Here, we introduce highly alkali-stable mono- and spirocyclic piperidine-based cations onto PS by first performing a superacid-mediated Friedel-Crafts alkylation using 2-(piperidine-4-yl)propane-2-ol. This is followed by quaternization of the piperidine rings either using iodomethane to produce N,N-di-Me piperidinium cations or by cyclo-quaternizations using 1,5-dibromopentane and 1,4-dibromobutane, resp., to obtain N-spirocyclic quaternary ammonium cations. Thus, it is possible to functionalize up to 27% of the styrene units with piperidine rings and subsequently achieve complete quaternization. The synthetic approach ensures that all of the sensitive β-hydrogens of the cations are present in ring structures to provide high stability. AEMs based on these polymers show high alk. stability and less than 5% ionic loss was observed by 1H NMR spectroscopy after 30 days in 2 M aqueous NaOH at 90°C. AEMs functionalized with N,N-di-Me piperidinium cations show higher stability than the ones carrying N-spirocyclic quaternary ammonium. Careful anal. of the latter revealed that the rings formed in the cyclo-quaternization are more prone to degrade via Hofmann elimination than the rings introduced in the Friedel-Crafts reaction. AEMs with an ion-exchange capacity of 1.5 mequiv g-1 reach a hydroxide conductivity of 106 mS cm-1 at 80°C under fully hydrated conditions. The AEMs are further tuned and improved by blending with polybenzimidazole (PBI). For example, an AEM containing 2 weight % PBI shows reduced water uptake and much improved robustness during handling and reaches 71 mS cm-1 at 80°C. The study demonstrates that the critical alk. stability of PS-containing AEMs can be significantly enhanced by replacing the benchmark benzyltrimethyl ammonium cations with N-alicyclic piperidine-based cations.

There is still a lot of research devoted to this compound(SMILES：BrCCCCCBr)SDS of cas: 111-24-0, and with the development of science, more effects of this compound(111-24-0) can be discovered.

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

COA of Formula: C6H5N5. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about A rapid and green synthetic approach for hierarchically assembled porous ZnO nanoflakes with enhanced catalytic activity. Author is Sinhamahapatra, Apurba; Giri, Arnab Kanti; Pal, Provas; Pahari, Sandip Kumar; Bajaj, Hari C.; Panda, Asit Baran.

Three dimensionally (3D) assembled hierarchical porous ZnO structures are of key importance for their applications in sensors, lithium-ion batteries, solar cells and in catalysis. Here, the controlled synthesis of 3D hierarchically porous ZnO architectures constructed of two dimensional (2D) nano-sheets through the calcination of a hydrozincite [Zn5(CO3)2(OH)6] intermediate is presented. The intermediate 3D hierarchical hydrozincite has been synthesized by a novel organic surfactant and solvent free aqueous protocol at room temperature using an aqueous solution of ammonium carbonate and laboratory grade bulk ZnO in a short time (20-30 min). The amount of carbonate and the reaction temperature play a crucial role in the formation of the 3D hierarchical morphol. and on the basis of the exptl. results a probable reaction mechanism is proposed. On calcination, the synthesized 3D hierarchical hydrozincite resulted in ZnO with an almost identical morphol. to the parental hydrozincite. On decomposition a porous structure having a surface area of 44 M2 g-1 is obtained. The synthesized hierarchical ZnO morphol. exhibits an improved catalytic activity for the synthesis of 5-substituted-1H-tetrazoles with different nitriles and sodium azide than that of nanocrystalline ZnO and bulk ZnO, as well as other developed solid catalysts. The catalyst is easily recyclable without a significant loss in catalytic activity.

There is still a lot of research devoted to this compound(SMILES：C1(C2=NN=NN2)=CC=NC=C1)COA of Formula: C6H5N5, and with the development of science, more effects of this compound(14389-12-9) can be discovered.

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.Wang, Wentian; Zhang, Lu; Morlock, Lorraine; Williams, Noelle S.; Shay, Jerry W.; De Brabander, Jef K. researched the compound: 2-Chloro-5-pyridinesulfonyl chloride( cas:6684-39-5 ).COA of Formula: C5H3Cl2NO2S.They published the article 《Design and Synthesis of TASIN Analogues Specifically Targeting Colorectal Cancer Cell Lines with Mutant Adenomatous Polyposis Coli (APC)》 about this compound( cas:6684-39-5 ) in Journal of Medicinal Chemistry. Keywords: preparation TASIN analog targeting colorectal cancer. We’ll tell you more about this compound (cas:6684-39-5).

Despite advances in targeted anticancer therapies, there are still no small-mol.-based therapies available that specifically target colorectal cancer (CRC) development and progression, the second leading cause of cancer deaths. We previously disclosed the discovery of truncating adenomatous polyposis coli (APC)-selective inhibitor 1 (TASIN-1), a small mol. that specifically targets colorectal cancer cells lines with truncating mutations in the adenomatous polyposis coli (APC) tumor suppressor gene through inhibition of cholesterol biosynthesis. Here, we report a medicinal chem. evaluation of a collection of TASIN analogs and activity against colon cancer cell lines and an isogenic cell line pair reporting on the status of APC-dependent selectivity. A number of potent and selective analogs were identified, including compounds with good metabolic stability and pharmacokinetic properties. The compounds reported herein represent a first-in-class genotype-selective series that specifically target apc mutations present in the majority of CRC patients and serve as a translational platform toward a targeted therapy for colon cancer.

There is still a lot of research devoted to this compound(SMILES：ClC1=NC=C(C=C1)[S](=O)(=O)Cl)COA of Formula: C5H3Cl2NO2S, and with the development of science, more effects of this compound(6684-39-5) can be discovered.

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

Category: chiral-nitrogen-ligands. 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: 1,5-Dibromopentane, is researched, Molecular C5H10Br2, CAS is 111-24-0, about Acetylcholinesterase inhibition of diversely functionalized quinolinones for alzheimer’s disease therapy.

The synthesis and cholinesterase (ChE)/monoamine oxidase (MAO) inhibition of quinolinones I [R = 2-diethylaminoethyl, 1-methyl-4-piperidyl, 3-morpholinopropyl, etc.] and dihydroquinolinones II [R1 = 1-methyl-4-piperidyl, 2-morpholinoethyl, 2-(4-isopropylpiperazin-1-yl)ethyl, etc.] designed as potential multitarget small mols. (MSM) for alzheimer’s disease therapy was reported.. None of them showed significant human recombinant MAO inhibition, but compounds I [R = 4-(4-isopropylpiperazin-1-yl)butyl, 5-(4-isopropylpiperazin-1-yl)pentyl] and compound II [R1 = 4-(4-isopropylpiperazin-1-yl)butyl] displayed promising human recombinant acetylcholinesterase (hrAChE) and butyrylcholinesterase (hrBuChE) inhibition. In particular, compound I [R = 4-(4-isopropylpiperazin-1-yl)butyl] was found to be a potent and quite selective non-competitive inhibitor of hrAChE (IC50 = 0.29μM), with Ki value in nanomolar range (79 nM). Pertinent docking anal. confirmed this result, suggesting that this ligand was an interesting hit for further investigation.

There is still a lot of research devoted to this compound(SMILES：BrCCCCCBr)Category: chiral-nitrogen-ligands, and with the development of science, more effects of this compound(111-24-0) can be discovered.

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

Name: 2-Chloro-5-pyridinesulfonyl chloride. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Chloro-5-pyridinesulfonyl chloride, is researched, Molecular C5H3Cl2NO2S, CAS is 6684-39-5, about An experimental and theoretical dipole moment study of 2-chloropyridine-5-sulfonyl chloride. Author is Lumbroso, H.; Montoneri, E.; Pappalardo, G. C..

Anal. of the dipole moment (2.00 D) of 2-chloropyridine-5-sulfonly chloride in benzene at 30° supported a model in which the C(5)-SCl group is rotated by 40° from the 2-chloro-1-pyridyl group. Such a model, with the S Cl atom close to the 1-azanitrogen atom, can be explained by interplay of 2 conflicting factors, namely sulfonylchloride-arene conjugation and lesser repulsion between 1 of the O atoms and the aza N atom.

There is still a lot of research devoted to this compound(SMILES：ClC1=NC=C(C=C1)[S](=O)(=O)Cl)Name: 2-Chloro-5-pyridinesulfonyl chloride, and with the development of science, more effects of this compound(6684-39-5) can be discovered.

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