Tag: 100-200

Ruthenium(II)-catalyzed ortho-C-H arylation of diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination was written by Nareddy, Pradeep;Jordan, Frank;Szostak, Michal. And the article was included in Organic & Biomolecular Chemistry in 2017.Formula: C12H11N This article mentions the following:

The first method for the direct, regioselective Ru(II)-catalyzed oxidative arylation of C-H bonds in diverse N-heterocycles, e.g., 1-phenyl-1H-pyrazole with aryl silanes 4-RC₆H₄Si(OMe)₃ (R = H, Me, Cl, etc.) by exploiting solvent-controlled N-coordination has been reported. The reaction takes advantage of the attractive features of organosilanes as coupling partners, providing proof of concept for N-directed Ru(II)-catalyzed C-H arylation. This novel, operationally-simple and versatile protocol utilizes the Ru(II)/CuF₂ reagent system in which CuF₂ serves as a dual activator/oxidant in non-coordinating solvents to accommodate for ligand N-coordination. This first Ru(II)-catalyzed N-directed Hiyama C-H arylation offers broad implications to achieve numerous C-H bond functionalizations by versatile ruthenium(II) catalysis manifold. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Formula: C12H11N).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 锜?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 锜?bonds. 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. Formula: C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Highly Regio- and Chemoselective Oxidative C-H/C-H Cross-Couplings of Anilines and Phenols Enabled by a Co-Oxidant-Free Rh(I)/Zn(NTf₂)₂/Air Catalytic System was written by Zhang, Luoqiang;Wang, Yanbing;Shi, Yang;Wu, Yimin;Lan, Jingbo;Ma, Weixin;You, Jingsong. And the article was included in ACS Catalysis in 2019.Electric Literature of C11H9NO This article mentions the following:

An urgent yet challenging task is to overcome the limitations in substrate scope and regio- and chemoselectivity in the oxidative couplings between two arenes for the construction of unsym. 2,2′-difunctional biaryls with diverse application requirements. In this work, a co-oxidant-free Rh(I)/Zn(NTf₂)₂/air catalytic system has been developed for dual chelation-assisted oxidative C-H/C-H cross-couplings between two anilines, between two phenols, and between phenols and anilines, which enables rapid assembly of rich libraries of 2,2′-bianilines, 2,2′-biphenols, and 2′-aminobiphenyl-2-ols. This protocol features air as the sole oxidant, complete regioselectivity, high chemoselectivity, low molar ratio of substrates (even 1:1), convenient operation, and scale-up synthesis. The established catalytic system is tolerant of the substrates having both electron-donating and electron-withdrawing substituents at different positions of the aryl ring. This work further discloses that the chemoselectivity of cross-coupling over homocoupling mainly relies on a suitable combination of two directing groups (i.e., a pair of strongly and weakly coordinating directing groups) rather than the electronically distinct properties between two substrates, which provides an inspiration for designing the matching directing group pair for the dual chelation-assisted oxidative Ar-H/Ar-H cross-couplings. Thus, this strategy allows the highly chemoselective cross-coupling between electronically similar coupling partners, which represents a challenging task in the oxidative Ar-H/Ar-H cross-coupling reactions. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Electric Literature of C11H9NO).

2-Phenoxypyridine (cas: 4783-68-0) 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. 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. Electric Literature of C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A simple one-pot synthesis of benzoxazine- 2,4-diones and benzothiazine-2,4-diones was written by Zhu, Xiaoxiang;Yu, Qian-Sheng;Greig, Nigel H.;Flippen-Anderson, Judith L.;Brossi, Arnold. And the article was included in Heterocycles in 2003.Application of 28020-37-3 This article mentions the following:

A simple and efficient procedure has been developed for a one-pot synthesis of substituted benzoxazine-2,4-diones and benzothiazine-2,4-diones directly from salicylic acid (or thiosalicylic acid) and amines. The reaction of [2-(chlorocarbonyl)phenyl]carbonic acid Me ester with 3,4-dimethoxybenzeneethanamine gave 2-(acetyloxy)-N-[2-(3,4-dimethoxyphenyl)ethyl]benzamide. Deprotection of this gave 2-hydroxy-N-[2-(3,4-dimethoxyphenyl)ethyl]benzamide and sequential cyclocondensation with carbonochloridic acid Et ester gave 3-[2-(3,4-dimethoxyphenyl)ethyl]-2H-1,3-benzoxazine-2,4(3H)-dione (I). A similar reaction sequence starting from 2-mercaptobenzoic acid gave 3-(phenylmethyl)-2H-1,3-benzothiazine-2,4(3H)-dione (II). In the experiment, the researchers used many compounds, for example, 3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3Application of 28020-37-3).

3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ璺痬ol閳? in pyridine vs. 150 kJ璺痬ol閳? in benzene). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application of 28020-37-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Determination of a new scale of ortho-steric parameters S⁰ from N-methylation of pyridines was written by Berg, Ulf;Gallo, Roger;Klatte, Gerd;Metzger, Jacques. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1980.Recommanded Product: 2-Phenoxypyridine This article mentions the following:

The kinetics of quaternization by MeI of 33 substituted pyridines, e.g. 2-ethylpyridine, were measured in MeCN at 30鎺? The relative rate constants obtained were similar to those observed in other polar aprotic solvents. The magnitude of steric effects observed for all ortho-substituents were estimated from the Broensted plot. A scale of ortho-steric parameters (S⁰) was proposed. No correlation was observed between S⁰ and the electronic effect of substituents. S⁰ Is not solvent dependent. The relative S⁰ values agree with other exptl. values of the steric size of the substituents. The S⁰ parameters are discussed in terms of substituent structure relative to the Taft-Kutter-Hansch E_s and Charton 璋?parameters. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Recommanded Product: 2-Phenoxypyridine).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ璺痬ol閳? in pyridine vs. 150 kJ璺痬ol閳? in benzene). 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.Recommanded Product: 2-Phenoxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A convenient synthesis of perfluoroalkylated indolizinylphosphonates was written by Shen, Yanchang;Zhang, Yuming;Jiang, Guo-Fang. And the article was included in Synthesis in 2002.HPLC of Formula: 17281-59-3 This article mentions the following:

A convenient method for the synthesis of perfluoroalkylated indolizinylphosphonates via the 1,3-cycloaddition of pyridinium N-ylides and perfluoroalkynylphosphonates in 49-77% yields is described. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3HPLC of Formula: 17281-59-3).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) 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. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.HPLC of Formula: 17281-59-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Facilitating Ir-Catalyzed C-H Alkynylation with Electrochemistry: Anodic Oxidation-Induced Reductive Elimination was written by Ye, Xiaohan;Wang, Chenhuan;Zhang, Shuyao;Wei, Jingwen;Shan, Chuan;Wojtas, Lukasz;Xie, Yan;Shi, Xiaodong. And the article was included in ACS Catalysis in 2020.SDS of cas: 4783-68-0 This article mentions the following:

An electrochem. approach in promoting directed C-H alkynylation with terminal alkyne via iridium catalysis is reported. This work employed anodic oxidation of Ir(III) intermediate (characterized by X-ray crystallog.) to promote reductive elimination, giving the desired coupling products in good yields (up to 95%) without the addition of any other external oxidants. This transformation is suitable for various directing groups with H₂ as the only byproduct, which warrants a high atom economy and practical oxidative C-C bond formation under mild conditions. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0SDS of cas: 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) 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. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.SDS of cas: 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pd-Catalyzed Diamination of 1,2,4-Triazinyl Complexant Scaffolds was written by Tai, Serene;Dover, Evan J.;Marchi, Sydney V.;Carrick, Jesse D.. And the article was included in Journal of Organic Chemistry in 2015.Safety of 4-Methylpicolinonitrile This article mentions the following:

As part of ongoing efforts in this laboratory to design and synthesize multidentate soft-N-donors as effective complexants for chemoselective minor actinide extraction from used nuclear fuel, a series of aminated mono-1,2,4-triazinylpyridines were required. This study focuses on streamlining convergent access to a diverse array of functionalized N-donors using Pd-catalysis from a common synthon affording access to pyridinyl triazines as the 4,4′-amino derivatives which are com. limited and unsuccessful in traditional condensation chem. A general Pd-catalyzed method for the double amination of functionalized pyridinyl-1,2,4-triazines with low catalyst/ligand loadings enabling the formation of 16 novel complexants is presented. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4Safety of 4-Methylpicolinonitrile).

4-Methylpicolinonitrile (cas: 1620-76-4) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Safety of 4-Methylpicolinonitrile

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and Utility of Dihydropyridine Boronic Esters was written by Panda, Santanu;Coffin, Aaron;Nguyen, Q. Nhu;Tantillo, Dean J.;Ready, Joseph M.. And the article was included in Angewandte Chemie, International Edition in 2016.Electric Literature of C11H17N This article mentions the following:

When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products. In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0Electric Literature of C11H17N).

4-Hexylpyridine (cas: 27876-24-0) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of 閳?8.7 鑴?10閳? cm3璺痬ol閳?.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ璺痬ol閳? in the liquid phase and 140.4 kJ璺痬ol閳? in the gas phase. 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. Electric Literature of C11H17N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

2-Aryl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols as a class of antitumor agents selectively active in securin^-/- cells was written by Zhang, Nan;Ayral-Kaloustian, Semiramis;Niu, Chuansheng;Nguyen, Thai;Upeslacis, Erik;Mansour, Tarek S.;Ragunathan, Shoba;Rosfjord, Edward. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.HPLC of Formula: 85838-94-4 This article mentions the following:

A series of 2-(4-aminophenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols have been developed as antitumor agents that showed high selectivity against aneuploid cell lines (vs diploid cell lines). Structure-activity relationship studies showed that a hydroxymethyl group at the 2-position of the Ph ring increased potency and selectivity. A pyrrolidinyl group at the 4-position of the Ph ring was comparable to a dimethylamino group. The corresponding 5-aza analogs, 2-(4-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-c]pyridin-7-ols, retained potency and high level of selectivity against aneuploid cell growth (vs diploid cells). These 5-aza compounds exhibited higher water solubility and higher metabolic stability than the corresponding carba analogs. Compound 19 (I) showed the highest potency against MCF-7 and MDA-MB-361 lines and was selected for further evaluation. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4HPLC of Formula: 85838-94-4).

tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) 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. 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: 85838-94-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and characterization of N-hydroxy-7-(3-substituted ureido)-4-(4-((4-(morpholinomethyl)phenyl)ethynyl)phenyl)-1,8-naphthyridine-2-carboxamides: a novel class of potential antibacterial, antifungal and anthelmintic agents was written by Prasad, V. Kamala;Sanjeeva, P.;Manjunath, G.;Rao, B. Subba;Ramana, P. Venkata. And the article was included in Heterocyclic Letters in 2022.Recommanded Product: N-(6-Aminopyridin-2-yl)acetamide This article mentions the following:

N-hydroxy-7-(3-substituted ureido)-4-(4-((4-(morpholinomethyl)phenyl)ethynyl) phenyl)-1,8-naphthyridine-2-carboxamides I [R = Et, i-Pr, Ph, etc.; R¹ = NHOH] were synthesized by treating Me 7-(3-substituted ureido)-4-(4-((4-(morpholinomethyl)phenyl)ethynyl) phenyl)-1,8-naphthyridine-2-carboxylate I [R¹ = OMe] with hydroxylamine in ethanol/THF. These newly synthesized 1,8-naphthyridine derivatives I were screened for their antibacterial, antifungal and anthelmintic activities against the resp. strains. The results showed that introduction of electron donating groups in the ureido moiety results in a significant decrease of antimicrobial activity and an increase in anthelmintic activity. In the experiment, the researchers used many compounds, for example, N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3Recommanded Product: N-(6-Aminopyridin-2-yl)acetamide).

N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 锜?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 锜?bonds. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Recommanded Product: N-(6-Aminopyridin-2-yl)acetamide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem