Tag: 100-200

Potassium Amide-Catalyzed Benzylic C-H Bond Addition of Alkylpyridines to Styrenes was written by Zhai, Dan-Dan;Zhang, Xiang-Yu;Liu, Yu-Feng;Zheng, Lei;Guan, Bing-Tao. And the article was included in Angewandte Chemie, International Edition in 2018.Formula: C8H11N This article mentions the following:

The benzylic functionalization of alkylpyridines is an important pathway for pyridine derivatives synthesis. The reaction partners, however, were mostly limited to highly reactive polar electrophiles. Herein, we report a potassium amide-catalyzed selective benzylic C-H bond addition of alkylpyridines to styrenes. Potassium bis(trimethylsilyl)amide (KHMDS), a readily available Bronsted base, showed excellent catalytic activity and chemoselectivity. A series of alkylpyridine derivatives, including benzylic quaternary carbon substituted pyridines, were obtained in good to high yield. Preliminary mechanistic studies revealed that the deprotonation equilibrium is probably responsible for the excellent selectivity. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Formula: C8H11N).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Formula: C8H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A simultaneous oxidation of isomeric benzyl- and isopropylpyridines was written by Opeida, I. A.;Matvienko, A. G.;Efimova, I. V.;Zalevskaya, N. M.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 1986.SDS of cas: 644-98-4 This article mentions the following:

A kinetic study was reported of the oxidation of the following binary mixture: (1) 3-isopropylpyridine with 2-, 3-, and 4-benzylpyridine and Ph₂CH₂; (2) 2-benzylpyridine with 2-, 3-, and 4-isopropylpyridine and cumene; and (3) 3-isopropylpyridine with 4-benzylpyridine. The reactivity of the isopropyl- and benzylpyridine increased in the order 4 < 2 < 3. Ph₂CH₂ was more reactive than the benzylpyridines, and cumene was more reactive than the isopropylpyridines. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4SDS of cas: 644-98-4).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. SDS of cas: 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides was written by Cristau, Henri-Jean;Cellier, Pascal P.;Spindler, Jean-Francis;Taillefer, Marc. And the article was included in Chemistry – A European Journal in 2004.Safety of 2-Phenoxypyridine This article mentions the following:

Mild, efficient, copper-catalyzed N-arylation procedures for nitrogen heterocycles, amides, carbamates, and C-arylation procedures for malonic acid derivatives have been developed that afford high yields of arylated products, e.g., I, with excellent selectivity. The N-arylation of imidazole with aryl bromides or iodides was found to be greatly accelerated by inexpensive, air-stable catalyst systems, combining catalytic copper salts or oxides with a set of structurally simple chelating ligands. The reaction was shown to be compatible with a broad range of aryl halides, encompassing sterically hindered, electron-poor, and electron-rich ones, providing the arylated products under particularly mild conditions. The lower limit in ligand and catalyst loading and the scope of Ullmann-type condensations catalyzed by complexes bearing those ligands with respect to the nucleophile class have also been investigated. Chelating Schiff base Chxn-Py-Al generated a remarkably general copper catalyst for N-arylation of pyrrole, indole, 1,2,4-triazole, amides, and carbamates; and C-arylation of di-Et malonate, Et cyanoacetate, and malononitrile with aryl iodides under mild conditions. The method reported here was successful with regard to Ullmann-type arylation. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Safety of 2-Phenoxypyridine).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Safety of 2-Phenoxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new chelation-assistance mode for a ruthenium-catalyzed silylation at the C-H bond in aromatic ring with hydrosilanes was written by Kakiuchi, Fumitoshi;Igi, Kimitaka;Matsumoto, Mitsutaka;Hayamizu, Tomoo;Chatani, Naoto;Murai, Shinji. And the article was included in Chemistry Letters in 2002.Related Products of 4783-68-0 This article mentions the following:

Ru-catalyzed reactions of aromatic compounds having an amino group or a heteroaromatic ring as a directing group with triethylsilane gave the corresponding ortho silylated products in good to excellent yields. E.g., 2-benzylpyridine reacts with HSiEt₃ in the presence of 6 mol% Ru₃(CO)₁₂ and norbornene/toluene to give 2-[2-(Et₃Si)C₆H₄]C₅H₄N (77% yield) or 2-[2,6-(Et₃Si)₂C₆H₃]C₅H₄N (13% yield). In contrast previous results, in which the reactive substrates with π-conjugation between the hetero atom in the directing group and the C atom possessing the C-H bond to be cleaved were used, the present reaction proceeds in cases of substrates having no such π-conjugation. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Related Products of 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Related Products of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A Novel Convenient Synthesis of Pyridinyl and Quinolinyl Triflates and Tosylates via One-Pot Diazotization of Aminopyridines and Aminoquinolines in Solution was written by Kassanova, Assiya Zh.;Krasnokutskaya, Elena A.;Beisembai, Perizat S.;Filimonov, Victor D.. And the article was included in Synthesis in 2016.Quality Control of 2-(m-Tolyl)pyridine This article mentions the following:

The first effective and simple method for the direct one-pot transformation of 2-, 3-, and 4-aminopyridines, 2,6-diaminopyridines, and 2-aminoquinoline into the corresponding pyridinyl and quinolinyl trifluoromethanesulfonates and tosylates in solvents was developed. The procedure involves diazotization of the heterocyclic amines with sodium nitrite in mixed hexane-DMSO or hexane-DMF solutions in the presence of trifluoromethanesulfonic acid or p-toluenesulfonic acid. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Quality Control of 2-(m-Tolyl)pyridine).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Quality Control of 2-(m-Tolyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Design of Conformationally Constrained Acyl Sulfonamide Isosteres: Identification of N-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)methane-sulfonamides as Potent and Selective hNa_V1.7 Inhibitors for the Treatment of Pain was written by Focken, Thilo;Chowdhury, Sultan;Zenova, Alla;Grimwood, Michael E.;Chabot, Christine;Sheng, Tao;Hemeon, Ivan;Decker, Shannon M.;Wilson, Michael;Bichler, Paul;Jia, Qi;Sun, Shaoyi;Young, Clint;Lin, Sophia;Goodchild, Samuel J.;Shuart, Noah G.;Chang, Elaine;Xie, Zhiwei;Li, Bowen;Khakh, Kuldip;Bankar, Girish;Waldbrook, Matthew;Kwan, Rainbow;Nelkenbrecher, Karen;Karimi Tari, Parisa;Chahal, Navjot;Sojo, Luis;Robinette, C. Lee;White, Andrew D.;Chen, Chien-An;Zhang, Yi;Pang, Jodie;Chang, Jae H.;Hackos, David H.;Johnson, J. P.;Cohen, Charles J.;Ortwine, Daniel F.;Sutherlin, Daniel P.;Dehnhardt, Christoph M.;Safina, Brian S.. And the article was included in Journal of Medicinal Chemistry in 2018.SDS of cas: 116922-60-2 This article mentions the following:

The sodium channel Na_V1.7 has emerged as a promising target for the treatment of pain based on strong genetic validation of its role in nociception. In recent years, a number of aryl and acyl sulfonamides have been reported as potent inhibitors of Na_V1.7, with high selectivity over the cardiac isoform Na_V1.5. Herein, we report on the discovery of a novel series of N-([1,2,4]triazolo[4,3-a]pyridin-3-yl)methanesulfonamides as selective Na_V1.7 inhibitors. Starting with the crystal structure of an acyl sulfonamide, we rationalized that cyclization to form a fused heterocycle would improve physicochem. properties, in particular lipophilicity. Our design strategy focused on optimization of potency for block of Na_V1.7 and human metabolic stability. Lead compounds I (R¹ = cPr, R² = Me), I (R¹ = cPr, R² = cPr) (GNE-131), and II showed excellent potency, good in vitro metabolic stability, and low in vivo clearance in mouse, rat, and dog. Compound I (R¹ = cPr, R² = cPr) also displayed excellent efficacy in a transgenic mouse model of induced pain. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluoropyridine (cas: 116922-60-2SDS of cas: 116922-60-2).

3-Bromo-4-fluoropyridine (cas: 116922-60-2) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.SDS of cas: 116922-60-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

From Pyridine-N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy was written by Bugaenko, Dmitry I.;Yurovskaya, Marina A.;Karchava, Alexander V.. And the article was included in Organic Letters in 2021.HPLC of Formula: 59718-84-2 This article mentions the following:

The reactions of pyridine-N-oxides with Ph₃P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalent This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operated at ambient temperature and tolerated sensitive functional groups, enabling the synthesis of otherwise challenging compounds In the experiment, the researchers used many compounds, for example, Methyl 3-methylpicolinate (cas: 59718-84-2HPLC of Formula: 59718-84-2).

Methyl 3-methylpicolinate (cas: 59718-84-2) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. HPLC of Formula: 59718-84-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Metal-Free Synthesis of C-4 Substituted Pyridine Derivatives Using Pyridine-boryl Radicals via a Radical Addition/Coupling Mechanism: A Combined Computational and Experimental Study was written by Wang, Guoqiang;Cao, Jia;Gao, Liuzhou;Chen, Wenxin;Huang, Wenhao;Cheng, Xu;Li, Shuhua. And the article was included in Journal of the American Chemical Society in 2017.Formula: C6H3FN2 This article mentions the following:

D. functional theory investigations revealed that the pyridine-boryl radical generated in situ using 4-cyanopyridine and bis(pinacolato)diboron could be used as a bifunctional “reagent”, which serves as not only a pyridine precursor but also a boryl radical. With the unique reactivity of such radicals, 4-substituted pyridine derivatives could be synthesized using α,β-unsaturated ketones and 4-cyanopyridine via a novel radical addition/C-C coupling mechanism. Several controlled experiments were conducted to provide supportive evidence for the proposed mechanism. In addition to enones, the scope could be extended to a wide range of boryl radical acceptors, including various aldehydes and ketones, aryl imines and alkynones. Lastly, this transformation was applied in the late-stage modification of a complicated pharmaceutical mol. In the experiment, the researchers used many compounds, for example, 2-Fluoroisonicotinonitrile (cas: 3939-14-8Formula: C6H3FN2).

2-Fluoroisonicotinonitrile (cas: 3939-14-8) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Formula: C6H3FN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Heterocyclic chalcone activators of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) with improved in vivo efficacy was written by Lounsbury, Nicole;Mateo, George;Jones, Brielle;Papaiahgari, Srinivas;Thimmulappa, Rajash K.;Teijaro, Christiana;Gordon, John;Korzekwa, Kenneth;Ye, Min;Allaway, Graham;Abou-Gharbia, Magid;Biswal, Shyam;Childers, Wayne. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Recommanded Product: 2-(Trifluoromethyl)nicotinaldehyde This article mentions the following:

Nrf2 activators represent a good drug target for designing agents to treat diseases associated with oxidative stress. Building upon previous work, we designed and prepared a series of heterocyclic chalcone-based Nrf2 activators with reduced lipophilicity and, in some cases, greater in vitro potency compared to the resp. carbocyclic scaffold. These changes resulted in enhanced oral bioavailability and a superior pharmacodynamic effect in vivo. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethyl)nicotinaldehyde (cas: 116308-35-1Recommanded Product: 2-(Trifluoromethyl)nicotinaldehyde).

2-(Trifluoromethyl)nicotinaldehyde (cas: 116308-35-1) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Recommanded Product: 2-(Trifluoromethyl)nicotinaldehyde

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

C-H···Anion Interactions Assisted Addition of Water to Glycals by Sterically Hindered 2,4,6-Tri-tert-butylpyridinium Hydrochloride was written by Mukherji, Ananya;Kancharla, Pavan K.. And the article was included in Organic Letters in 2020.HPLC of Formula: 628-13-7 This article mentions the following:

The conjugate acid of the bulky base 2,4,6-tri-tert-butylpyridine, under mild conditions, catalyzes the synthesis of silyl-protected 2-deoxy-hemiacetals and their dimerized products from glycals at varying concentrations of water. The criticality of the concentration of water in the reaction outcome is indicative of a unique mechanistic pathway for the bulky pyridine salt and not via the general Bronsted acid mechanism. The various silyl-protected hemiacetals thus synthesized were successfully utilized in the stereoselective synthesis of both α and β glycosides. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7HPLC of Formula: 628-13-7).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.HPLC of Formula: 628-13-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem