Month: January 2023

TBHP promoted demethylation of α-amino carbonyl compounds: a concise approach to substituted γ-lactams was written by Peng, Xue;Wang, Hui-Hong;Cao, Fei;Zhang, Hong-Hua;Lu, Ying-Mei;Hu, Xiao-Ling;Tan, Wen;Wang, Zhen. And the article was included in Organic Chemistry Frontiers in 2019.Quality Control of tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate This article mentions the following:

A novel tert-Bu hydroperoxide (TBHP) promoted CH₂-extrusion reaction of α-amino carbonyl compounds I (R = Me, naphthalen-2-ylmethyl, Bn, cyclopropyl, etc.; R¹ = H, Me, Et, Br; R² = H, (CH₃)₂; R³ = H, Me; R¹R³ = -CH=CH-CH=CH-; A = (CHR³)_1-2; R⁴ = H, Me, allyl, Bn) has been developed, which is driven by a demethylenation process to give various ring contraction products γ-lactams II under radical conditions. The reaction shows good functional group tolerance and excellent chemo/regioselectivity; all the desired products are obtained in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Quality Control of tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate).

tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) 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. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Quality Control of tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Solvent Selection Scheme Using Machine Learning Based on Physicochemical Description of Solvent Molecules: Application to Cyclic Organometallic Reaction was written by Fujinami, Mikito;Maekawara, Hiroki;Isshiki, Ryota;Seino, Junji;Yamaguchi, Junichiro;Nakai, Hiromi. And the article was included in Bulletin of the Chemical Society of Japan in 2020.Name: 2-Phenoxypyridine This article mentions the following:

A solvent selection scheme for optimization of reactions is proposed using machine learning, based on the numerical descriptions of solvent mols. Twenty-eight key solvents were represented using 17 physicochem. descriptors. Clustering anal. results implied that the descriptor represents the chem. characteristics of the solvent mols. During the assessment of an organometallic reaction system, the regression anal. indicated that learning even a small number of exptl. results can be useful for identifying solvents that will produce high exptl. yields. Observation of the regression coefficients, and both clustering and regression anal., can be effective when selecting a solvent to be used for an experiment In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Name: 2-Phenoxypyridine).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Toward the Total Synthesis of Alpkinidine: Synthesis of Haloquinone CE Ring System Synthons and Attempted Nucleophilic Bisannulation was written by Buccini, Marco;Tham, Louisa;Dhoro, Francis;Skelton, Brian W.;Williams, Craig M.;Piggott, Matthew J.. And the article was included in ACS Omega in 2022.Reference of 628-13-7 This article mentions the following:

Model chem. involving the bisannulation of 2,3-dichloro-1,4-naphthoquinone with the ester enolate derived from Et ester of o-nitrophenylacetic acid, which rapid assembled the ABCD ring system of a pentacyclic pyrroloacridine, has been applied to the attempted synthesis of the marine natural product alpkinidine. The reaction of Et ester of o-nitrophenylacetic acid with 6,7-dichloro-2-methylisoquinoline-1,5,8(2H)-trione, required to extend the model strategy to alpkinidine, was unfruitful, giving only complex mixtures Efforts to direct the regiochem. of the key Michael substitution step using 6-bromo-2-methylisoquinoline-1,5,8(2H)-trione afforded an adduct sharing the complete carbon skeleton of alpkinidine, but this could not be elaborated to the natural product. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Reference of 628-13-7).

Pyridinehydrochloride (cas: 628-13-7) 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. 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.Reference of 628-13-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Polystyrene-supported Pd(II) complex-catalysed carboacylation of 2-arylpyridines with alcohols via C-H bond activation under solvent-free conditions was written by Perumgani, Pullaiah C.;Parvathaneni, Sai Prathima;Keesara, Srinivas;Mandapati, Mohan Rao. And the article was included in Applied Organometallic Chemistry in 2017.Related Products of 4373-61-9 This article mentions the following:

Polystyrene-supported N,N-dimethylethylenediamine Pd(II) complex was used as an efficient catalyst for the synthesis of aromatic ketones via ortho-acylation of sp² C-H bonds of 2-arylpyridines with alcs. as effective coupling partners. The alcs. were oxidized with tert-Bu hydroperoxide to their corresponding aldehydes in situ and efficiently coupled with 2-arylpyridines to form aryl ketones under solvent-free conditions. Furthermore, the catalyst could be easily recovered by simple filtration and reused for five cycles without any significant decrease in its activity. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Related Products of 4373-61-9).

2-(m-Tolyl)pyridine (cas: 4373-61-9) 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). Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Related Products of 4373-61-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rhoda-Electrocatalyzed C-H Methylation and Paired Electrocatalyzed C-H Ethylation and Propylation was written by Kucinski, Krzysztof;Simon, Hendrik;Ackermann, Lutz. And the article was included in Chemistry – A European Journal in 2022.Synthetic Route of C12H11N This article mentions the following:

Herein, the rhoda-electrocatalyzed C-H activation/alkylation of several N-heteroarenes was described. This catalytic approach was successfully applied to several arenes, including biol. relevant purines, diazepam, and amino acids. The versatile C-H alkylation featured water as a co-solvent and user-friendly trifluoroborates as alkylating agents. Finally, the rhoda-electrocatalysis with unsaturated organotrifluoroborates proceeded by paired electrolysis. 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. 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Synthetic Route of C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of pyrrolopyridines (azaindoles) was written by Mahadevan, Indumathy;Rasmussen, Malcolm. And the article was included in Journal of Heterocyclic Chemistry in 1992.Recommanded Product: 3,6-Dimethyl-2-pyridinamine This article mentions the following:

Improved, convenient, and reliable routes for the synthesis of 4-, 5-, 6-, and 7-azaindole, 7-methyl-4-azaindole, 7-methyl-6-azaindole, and the hitherto unreported 7-amino-4-azaindole are described. The synthesis have been accomplished either by significant modifications to established procedures or by new methods which afford the compounds in improved yields. Thus, 2-chloro-4-methyl-3- and 5-nitropyridines condensed with Me₂NCH(OMe)₂ followed by hydrogenation to give 6-azaindole I in 75% yield. In the experiment, the researchers used many compounds, for example, 3,6-Dimethyl-2-pyridinamine (cas: 823-61-0Recommanded Product: 3,6-Dimethyl-2-pyridinamine).

3,6-Dimethyl-2-pyridinamine (cas: 823-61-0) 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: 3,6-Dimethyl-2-pyridinamine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols was written by Colgan, Avene C.;Proctor, Rupert S. J.;Gibson, David C.;Chuentragool, Padon;Lahdenpera, Antti S. K.;Ermanis, Kristaps;Phipps, Robert J.. And the article was included in Angewandte Chemie, International Edition in 2022.Related Products of 644-98-4 This article mentions the following:

Catalytic enantioselective Minisci reactions have recently been developed but all instances so far utilize α-amino radical coupling partners. Authors report a substantial evolution of the enantioselective Minisci reaction that enables α-hydroxy radicals to be used, providing valuable enantioenriched secondary alc. products. This is achieved through the direct oxidative coupling of two C-H bonds on simple alc. and pyridine partners through a hydrogen atom transfer (HAT)-driven approach: a challenging process to achieve due to the numerous side reactions that can occur. This approach is highly regioselective as well as highly enantioselective. Dicumyl peroxide, upon irradiation with 390 nm light, serves as both HAT reagent and oxidant while selectivity is controlled by use of a chiral phosphoric acid catalyst. Computational and exptl. evidence provide mechanistic insight as to the origin of selectivity, revealing a stereodetermining deprotonation step distinct from the analogous reaction of amide-containing substrates. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Related Products of 644-98-4).

2-Isopropylpyridine (cas: 644-98-4) 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. Related Products of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Anti-Markovnikov hydro(amino)alkylation of vinylarenes via photoredox catalysis was written by Wu, Zhao;Gockel, Samuel N.;Hull, Kami L.. And the article was included in Nature Communications in 2021.Safety of Phenyl(pyridin-2-yl)methanone This article mentions the following:

Herein, the application of this powerful catalytic manifold to address the hydroalkylation and hydroaminoalkylation of electronically diverse vinylarenes e.g., 1,1-diphenylethylene was presented. This reaction allows for generalized alkene hydroalkylation leveraging common alkyl radical precursors, such as organotrifluoroborate salts and carboxylic acids. Furthermore, utilizing easily accessible α-silyl amine reagents or tertiary amines directly, secondary and tertiary amine moieties can be installed onto monoaryl and diaryl alkenes to access valuable products. Thus, under a unified system, both hydroalkylation and hydroaminoalkylation of alkenes are achieved. The substrate scope is evaluated through 57 examples, the synthetic utility of the method is demonstrated, and preliminary mechanistic insights are presented. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Safety of Phenyl(pyridin-2-yl)methanone).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) 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). 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.Safety of Phenyl(pyridin-2-yl)methanone

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Stereochemical studies of heterocyclic compounds. XII. Crystal and molecular structure of 1-(2-amino-1-cyano-2-thioethenyl)pyridinium ylides was written by Fischer, E.;Knippel, M.;Wollin, K. M.;Kalman, A.;Argay, G.. And the article was included in Journal fuer Praktische Chemie (Leipzig) in 1983.Recommanded Product: 1-(Cyanomethyl)pyridin-1-ium chloride This article mentions the following:

E/Z Isomerization and hindered rotation of the pyridine ring were examined in I (R = Me, R¹ = Et). The former process had ΔG^* = 67 kJ/mol; the latter had ΔG^* = 46 kJ/mol. Crystallog. data, bond lengths, and bond angles were determined for I (R = H, R¹ = Ph); both E and Z isomers exists in the crystal. The C:C double bond is considerably longer than those in some olefins. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Recommanded Product: 1-(Cyanomethyl)pyridin-1-ium chloride).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) 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). 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: 1-(Cyanomethyl)pyridin-1-ium chloride

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The interaction between ionic liquids (ILs) and an enriched ammonia oxidising bacteria (AOB) culture was written by Chua, Feng Jun Desmond;Yan, Wangwang;Zhou, Yan. And the article was included in Chemosphere in 2019.Application of 104-73-4 This article mentions the following:

Ionic liquids (ILs) have attracted attention in recent years due to their ”greener” properties compared to conventional organic solvents. However, they may still pose a risk to the environment as their toxicity is not fully understood. Bioremediation of such ILs can be an economically and environmentally friendly approach. Therefore, this study aims to examine the interaction of three ILs (1-dodecylpyridnium chloride [DPy]⁺Cl, 1-Butyl-3-methylimidazolium chloride [BMIm]⁺Cl, and 1-Carbamoylmethyl pyridinium chloride [CMPy]⁺Cl) at different concentrations with an enriched ammonia oxidizing bacteria (AOB) culture, and investigate their effects on the ammonia oxidation rate (AOR) as well as their removal and transformation. The results indicated that the longer chain IL [DPy]⁺Cl had a neg. effect on the AOR while [BMIm]⁺Cl and [CMPy]⁺Cl enhanced the AOR. However, the IL removal rates displayed the opposite results as [DPy]⁺Cl was observed with the highest removal. It was found that biosorption played a major role in [DPy]⁺Cl removal. Biotransformation products for each IL were identified and their pathways were proposed. This study demonstrated that although longer chain ILs have a greater degree of removal, and they are also more toxic to AOB at higher concentration In the experiment, the researchers used many compounds, for example, 1-Dodecylpyridin-1-ium bromide (cas: 104-73-4Application of 104-73-4).

1-Dodecylpyridin-1-ium bromide (cas: 104-73-4) 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. 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.Application of 104-73-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem