Day: January 30, 2023

Rhodium-Catalyzed CxS and CxN Functionalization of Arenes: Combination of CxH Activation and Hypervalent Iodine Chemistry was written by Wang, Fen;Yu, Xinzhang;Qi, Zisong;Li, Xingwei. And the article was included in Chemistry – A European Journal in 2016.Synthetic Route of C12H11N This article mentions the following:

Rhodium-catalyzed sulfonylation, thioetherification, thiocyanation, and other heterofunctionalizations of arenes bearing a heterocyclic directing group were realized. The reaction proceeds by initial Rh^III-catalyzed CxH hyperiodination of arene at room temperature followed by uncatalyzed nucleophilic functionalization. A diaryliodonium salt was isolated as an intermediate, which represents umpolung of the arene substrate, in contrast to previous studies that suggested umpolung of the coupling partner. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Synthetic Route of C12H11N).

2-(m-Tolyl)pyridine (cas: 4373-61-9) 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.Synthetic Route of C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kinetics of the reaction of diphenylphosphinic hydrazide with phenyl isothiocyanate in the presence of benzopyridines was written by Yanchuk, N. I.. And the article was included in Zhurnal Obshchei Khimii in 1986.Application of 644-98-4 This article mentions the following:

The catalytic activity of pyridines and benzopyridines in the reaction of Ph₂P(O)NHNH₂ with PhNCS to give Ph₂P(O)NHNHCSNHPh decreased in the following order: isoquinoline > pyridine > 2,4-dimethypyridine > 2,4,6-trimethylpyrdine > 2-ethylpyridine > 2-picoline > quinoline > 2-isopropylpyridine > acridine > 2,6-dimethylpyridine > quinaldine. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Application of 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Anticancer activity of novel pyrido[2,3-b]indolizine derivatives: the relevance of phenolic substituents was written by Boot, Arnoud;Brito, Alexandra;Van Wezel, Tom;Morreau, Hans;Costa, Marta;Proenca, Fernanda. And the article was included in Anticancer Research in 2014.Formula: C7H7ClN2 This article mentions the following:

Background/Aim: The potential of indolizine derivatives as anticancer agents has been shown through recent studies. Herein, we present our exptl. results, showing that pyrido[2,3-b]indolizine derivatives are effective against colorectal cancer (CRC) cell lines. Materials and Methods: Several pyrido[2,3-b]indolizine derivatives were synthesized and their anticancer potential was evaluated against three CRC cell lines and two normal fibroblast cultures. Results: Our experiments identified 4-(3,4)-dihydroxyphenyl)-2-phenylpyrido[2,3-b]indolizine-10-carbonitrile (4f) as being active against all CRC cell lines at concentrations non-cytotoxic against fibroblast cultures. Addnl., cell-cycle anal. indicated that pyrido[2,3-b]indolizines can affect cell-cycle progression, with treated cells accumulating in the S- and G₂/M-phase. Conclusion: The hydroxyl groups in both the 3- and 4- positions of the aromatic substituent on C4 of the indolizine nucleus are crucial for activity against CRC cell lines. Further manipulation of the number and position of hydroxyl substituents on the aromatic rings may lead to improved anticancer activity of this class of compounds In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Formula: C7H7ClN2).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Formula: C7H7ClN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Switching the Reactivity of the Nickel-Catalyzed Reaction of 2-Pyridones with Alkynes: Easy Access to Polyaryl/Polyalkyl Quinolinones was written by Prusty, Namrata;Mohanty, Smruti Ranjan;Banjare, Shyam Kumar;Nanda, Tanmayee;Ravikumar, Ponneri C.. And the article was included in Organic Letters in 2022.Product Details of 626-64-2 This article mentions the following:

A Ni-catalyzed C6 followed by C5 cascade C-H activation/[2 + 2 + 2] annulation of 2-pyridone with alkynes has been achieved. A change in the reaction pathway was achieved by tuning the reaction conditions and incorporating a directing group. A wide variety of substrates and alkynes are amenable to this transformation. The key to success for this transformation is the use of sodium iodide as an additive. More importantly, authors detected the five-membered metallacycle intermediate through HRMS wherein iodide is ligated to the metal. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Product Details of 626-64-2).

Pyridin-4-ol (cas: 626-64-2) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. 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. Product Details of 626-64-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Correlation and Estimation of Gas-Chloroform and Water-Chloroform Partition Coefficients by a Linear Free Energy Relationship Method was written by Abraham, Michael H.;Platts, James A.;Hersey, Anne;Leo, Albert J.;Taft, Robert W.. And the article was included in Journal of Pharmaceutical Sciences in 1999.COA of Formula: C11H17N This article mentions the following:

A linear free energy relation, LFER, has been used to correlate 150 values of gas-chloroform partition coefficients, as log L^chl with a standard deviation, sd, of 0.23 log units, a correlation coefficient r² of 0.985, and an F-statistic of 1919. The equation reveals that bulk chloroform is dipolar/polarizable, of little hydrogen-bond basicity, but as strong a hydrogen-bond acid as bulk methanol or bulk ethanol. However, the main influence on gaseous solubility in chloroform is due to solute-solvent London dispersion interactions. A slightly modified LFER has been used to correlate 302 values of water-chloroform partition coefficients, as log P_chl. The correlation equation predicts log P_chl for a further 34 compounds not used in the equation with sd = 0.17 log units. When the LFER is applied to all 335 log P_chl values, the resulting equation has sd = 0.25, r² = 0.971, and F = 2218. The importance of these results lies in the recent use of the water-chloroform system as a measure of solute lipophilicity and of recent calculations of the transfer of nucleic acids from water to chloroform. Furthermore if the water-chloroform system is to be generally used as a measure of solute lipophilicity in drug design, it will be of very considerable help to have a predictive procedure available. The authors have shown that the multiple linear regression anal. (MLRA) method is capable of correlating log P_chl values rather better than computational methods although the present MLRA method suffers from the possible lack of availability of the required descriptors. In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0COA of Formula: C11H17N).

4-Hexylpyridine (cas: 27876-24-0) 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.COA of Formula: C11H17N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and biological evaluation of thiazole derivatives as GPR119 agonists was written by Kim, Hyojin;Cho, Suk Joon;Yoo, Minjin;Kang, Seung Kyu;Kim, Kwang Rok;Lee, Hwan Hee;Song, Jin Sook;Rhee, Sang Dal;Jung, Won Hoon;Ahn, Jin Hee;Jung, Jae-Kyung;Jung, Kwan-Young. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Electric Literature of C11H20N2O2S This article mentions the following:

A series of 4-(phenoxymethyl)thiazole derivatives was synthesized and evaluated for their GPR119 agonistic effect. Several 4-(phenoxymethyl)thiazoles with pyrrolidine-2,5-dione moieties showed potent GPR119 agonistic activities. Among them, compound I (R = F, Me) showed good in vitro activity with an EC₅₀ value of 49 nM and 18 nM, resp. with improved human and rat liver microsomal stability compare with MBX-2982. Compound I (R = F, Me) did not exhibit significant CYP inhibition, hERG binding, and cytotoxicity. Moreover, these compounds lowered the glucose excursion in mice in an oral glucose-tolerance test. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (cas: 214834-18-1Electric Literature of C11H20N2O2S).

tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (cas: 214834-18-1) 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. 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.Electric Literature of C11H20N2O2S

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Alkylation of ambident 2-phenyl-1,3-indandione anion in ionic liquid medium and structure of alkylation products was written by Zicmanis, A.;Ozolina, A.;Mekss, P.;Klavins, M.. And the article was included in Latvijas Kimijas Zurnals in 2006.Synthetic Route of C17H30BrN This article mentions the following:

Alkylation of 2-phenyl-1,3-indandione anion by allyl bromide or propargyl chloride was faster in the ionic liquid 1-dodecylpyridinium bromide than in a phase-transfer system. Only C-alkylation products were formed, and the cation used had no appreciable effect. In the experiment, the researchers used many compounds, for example, 1-Dodecylpyridin-1-ium bromide (cas: 104-73-4Synthetic Route of C17H30BrN).

1-Dodecylpyridin-1-ium bromide (cas: 104-73-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Synthetic Route of C17H30BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Selective imaging of hydrogen peroxide over peroxynitrite by a boronate-based fluorescent probe engineered via a doubly activated electrophilicity-increasing strategy was written by Tian, Di-Hua;Liu, Jun-Ru;Wang, Si-Yuan;Yan, Shuai;Chai, Zuo-Hu;Dai, Fang;Zhang, Shengxiang;Zhou, Bo. And the article was included in Sensors and Actuators, B: Chemical in 2022.Formula: C5H6ClN This article mentions the following:

Boronate-based fluorescent probes are widely used for the imaging of hydrogen peroxide (H₂O₂). However, their selectivity might be subjected to the interference of other reactive oxygen species, especially peroxynitrite (ONOO^–), due to the reaction of boronates with ONOO^– being several orders of magnitude faster than with H₂O₂. This work highlights a doubly activated electrophilicity-increasing strategy to develop a boronate-based fluorescent probe THMP for selective imaging of H₂O₂ over ONOO^–, where a boronate-modified pyridiniumylacrylonitrile is grafted on the 2-(2′-hydroxy-3′-methoxyphenyl) benzothiazole scaffold. Specifically, the boronate oxidation of THMP by H₂O₂ leads to the release of the free fluorophore THMP-N, triggering a ratiometric fluorescence response from red to green. The presence of a doubly activated electrophilic site on the carbon-carbon double bond of THMP, by both the strong electron-withdrawing cyano group and the pyridinium moiety, allows selective oxidative cleavage of the double bond by ONOO^– to an aldehyde HMBT-CHO, thereby excluding the interference of ONOO^– in monitoring H₂O₂. With the aid of the probe, we successfully visualized increased levels of H₂O₂ during ferroptosis of HepG2 cells, and burst of H₂O₂ in brains of live mice during cerebral ischemia reperfusion injury. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Formula: C5H6ClN).

Pyridinehydrochloride (cas: 628-13-7) 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. 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.Formula: C5H6ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pyridine hydrochloride-catalyzed thiolation of alkenes: divergent synthesis of allyl and vinyl sulfides was written by Liu, Shiwen;Wang, Lili;Ma, Zhipeng;Zeng, Xiaojun;Xu, Bo. And the article was included in Organic Chemistry Frontiers in 2020.Quality Control of Pyridinehydrochloride This article mentions the following:

A highly efficient and practical protocol for the synthesis of allylic and vinyl sulfides via pyridinium chloride-catalyzed tandem thiolation-elimination of alkenes was described. This tandem protocol offered easy access to both allylic and 1,1-diarylvinyl sulfides under mild conditions with good to excellent yields and excellent functional group tolerance. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Quality Control of Pyridinehydrochloride).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). 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. Quality Control of Pyridinehydrochloride

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Introducing an α-Keto Ester Functional Group through Pt-Catalyzed Direct C-H Acylation with Ethyl Chlorooxoacetate was written by Javed, Erman;Guthrie, Jacob D.;Neu, Justin;Chirayath, George S.;Huo, Shouquan. And the article was included in ACS Omega in 2020.Related Products of 4783-68-0 This article mentions the following:

Platinum-catalyzed selective C-H acylation of 2-aryloxypyridines with Et chlorooxoacetate provided an efficient way of introducing an α-keto ester functional group. The reaction is oxidant-free, additive-free and more significantly free of any decarbonylative side reactions. The reaction tolerated a variety of substituents from strongly electron-donating to strongly electron-withdrawing groups. Double acylation was feasible for 2-phenoxypyridine and its derivatives with only one substituent at the para position. Although the reaction of 2-(2-methylphenoxy)pyridine with Et malonyl chloride did not produce the desired β-keto ester, the reaction with Et succinyl chloride proceeded smoothly to give the γ-keto ester. Et chlorooxoacetate was much more reactive than Et succinyl chloride in this Pt-catalyzed C-H acylation reaction. 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. 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. 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. Related Products of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem