Tag: 100-200

Tetramethylammonium Fluoride Alcohol Adducts for S_NAr Fluorination was written by Morales-Colon, Maria T.;See, Yi Yang;Lee, So Jeong;Scott, Peter J. H.;Bland, Douglas C.;Sanford, Melanie S.. And the article was included in Organic Letters in 2021.SDS of cas: 3939-12-6 This article mentions the following:

Nucleophilic aromatic fluorination (S_NAr) is among the most common methods for the formation of C(sp²)-F bonds. Despite many recent advances, a long-standing limitation of these transformations was the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alc. adducts (Me₄NF·ROH) as fluoride sources for S_NAr fluorination. Through systematic tuning of the alc. substituent (R), tetramethylammonium fluoride tert-amyl alc. (Me₄NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for S_NAr fluorination under mild and convenient conditions (80°C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles was demonstrated. In the experiment, the researchers used many compounds, for example, 6-Fluoronicotinonitrile (cas: 3939-12-6SDS of cas: 3939-12-6).

6-Fluoronicotinonitrile (cas: 3939-12-6) 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.SDS of cas: 3939-12-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen was written by Yu, Tao;Guo, Mingqing;Wen, Simiaomiao;Zhao, Rongrong;Wang, Jinlong;Sun, Yanli;Liu, Qixing;Zhou, Haifeng. And the article was included in RSC Advances in 2021.Product Details of 91-02-1 This article mentions the following:

A simple and practical oxidative scission of aromatic olefins to carbonyl compounds R¹C(O)R₂ [R¹ = Ph, 4-MeC₆H₄, 4-FC₆H₄, etc., R² = Ph, 4-MeOC₆H₄, 4-ClC₆H₄, ect.] using O₂ as the sole oxidant with poly(ethylene glycol) di-Me ether as a benign solvent was developed. A wide range of monosubstituted, gem-disubstituted, 1,2-disubstituted, trisubstituted and tetrasubstituted aromatic olefins was successfully converted into the corresponding aldehydes and ketones in excellent yields even with gram-scale reaction. Some control experiments were also conducted to support a possible reaction pathway. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Product Details of 91-02-1).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) 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 derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Product Details of 91-02-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Anhydrous Tetramethylammonium Fluoride for Room-Temperature S_NAr Fluorination was written by Schimler, Sydonie D.;Ryan, Sarah J.;Bland, Douglas C.;Anderson, John E.;Sanford, Melanie S.. And the article was included in Journal of Organic Chemistry in 2015.Reference of 3939-12-6 This article mentions the following:

This paper describes the room-temperature S_NAr fluorination of aryl halides and nitroarenes using anhydrous tetramethylammonium fluoride (NMe₄F). This reagent effectively converts aryl-X (X = Cl, Br, I, NO₂, OTf) to aryl-F under mild conditions (often room temperature). Substrates for this reaction include electron-deficient heteroaromatics (22 examples) and arenes (5 examples). The relative rates of the reactions vary with X as well as with the structure of the substrate. However, in general, substrates bearing X = NO₂ or Br react fastest. In all cases examined, the yields of these reactions are comparable to or better than those obtained with CsF at elevated temperatures (i.e., more traditional halex fluorination conditions). The reactions also afford comparable yields on scales ranging from 100 mg to 10 g. A cost anal. is presented, which shows that fluorination with NMe₄F is generally more cost-effective than fluorination with CsF. In the experiment, the researchers used many compounds, for example, 6-Fluoronicotinonitrile (cas: 3939-12-6Reference of 3939-12-6).

6-Fluoronicotinonitrile (cas: 3939-12-6) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Reference of 3939-12-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ruthenium(II)-Catalyzed C-H Acyloxylation of Phenols with Removable Auxiliary was written by Raghuvanshi, Keshav;Rauch, Karsten;Ackermann, Lutz. And the article was included in Chemistry – A European Journal in 2015.Product Details of 4783-68-0 This article mentions the following:

Intermol. C-H acyloxylations of phenols with removable directing groups were accomplished with a versatile ruthenium catalyst. Specifically, a cationic ruthenium(II) complex, formed in-situ, enabled the chemoselective C-H oxygenations of a broad range of substrates. The catalyst proved tolerant of synthetically valuable functional groups, and the substrate scope included both (hetero)aromatic and, the more challenging, aliphatic carboxylic acids. The proposed reaction mechanism involved a reversible C-H ruthenation and an oxidatively induced C-O-bond-forming reductive elimination. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Product Details of 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. 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.Product Details of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Optimal design of ionic liquids for thermal energy storage was written by Mehrkesh, Amirhossein;Karunanithi, Arunprakash T.. And the article was included in Computers & Chemical Engineering in 2016.Formula: C5H6ClN This article mentions the following:

Ionic liquids (ILs) are an emerging group of chems. which, with their tunable physicochem. properties, exhibit promise for use as novel materials in many applications. Thermal (e.g. solar) energy storage (TES) is one such area where they show potential to be thermally stable at high temperatures and store high amount of heat energy. A large number of ILs, through the combination of different cations and anions, can be potentially synthesized thereby presenting a good platform for design. However, since it is not possible to study this large number of compounds exptl. it is necessary to use computational methods to evaluate them. In this article, we present a computer-aided framework to design task-specific ionic liquids (ILs), using structure-property models and optimization methods. Thermal energy storage d. (capacity) was used as a measure of the ability of an IL to store thermal (solar) energy. An hydroxyl functionalized imidazolium-based IL, [3-hydroxy-imidazolium]⁺[BF4] ^–, was found to be the optimal candidate with highest thermal energy storage capacity along with appropriate m.p. and decomposition temperature 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. 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.Formula: C5H6ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Structure-Based Design and Synthesis of Potent, Ethylenediamine-Based, Mammalian Farnesyltransferase Inhibitors as Anticancer Agents was written by Fletcher, Steven;Keaney, Erin Pusateri;Cummings, Christopher G.;Blaskovich, Michelle A.;Hast, Michael A.;Glenn, Matthew P.;Chang, Sung-Youn;Bucher, Cynthia J.;Floyd, Ryan J.;Katt, William P.;Gelb, Michael H.;Van Voorhis, Wesley C.;Beese, Lorena S.;Sebti, Said M.;Hamilton, Andrew D.. And the article was included in Journal of Medicinal Chemistry in 2010.Formula: C6H3FN2 This article mentions the following:

A potent class of anticancer, human farnesyltransferase (hFTase) inhibitors has been identified by “piggy-backing” on potent, antimalarial inhibitors of Plasmodium falciparum farnesyltransferase (PfFTase). On the basis of a 4-fold substituted ethylenediamine scaffold, the inhibitors are structurally simple and readily derivatized, facilitating the extensive structure-activity relationship (SAR) study reported herein. The most potent inhibitor is compound I, which exhibited an in vitro hFTase IC₅₀ value of 25 nM and a whole cell H-Ras processing IC₅₀ value of 90 nM. Moreover, it is noteworthy that several of the inhibitors proved highly selective for hFTase (up to 333-fold) over the related prenyltransferase enzyme geranylgeranyltransferase-I (GGTase-I). A crystal structure of inhibitor II co-crystallized with farnesyl pyrophosphate (FPP) in the active site of rat FTase illustrates that the para-benzonitrile moiety of II is stabilized by a π-π stacking interaction with the Y361β residue, suggesting a structural explanation for the observed importance of this component of our inhibitors. In the experiment, the researchers used many compounds, for example, 6-Fluoronicotinonitrile (cas: 3939-12-6Formula: C6H3FN2).

6-Fluoronicotinonitrile (cas: 3939-12-6) 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. 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.Formula: C6H3FN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Palladium-Catalyzed ortho-Sulfonylation of 2-Aryloxypyridines and Subsequent Formation of ortho-Sulfonylated Phenols was written by Xu, Yinfeng;Liu, Ping;Li, Shun-Li;Sun, Peipei. And the article was included in Journal of Organic Chemistry in 2015.Synthetic Route of C11H9NO This article mentions the following:

A palladium-catalyzed direct sulfonylation of 2-aryloxypyridines on the ortho-position of the benzene ring was developed using 2-pyridyloxyl as the directing group and sulfonyl chlorides as sulfonylation reagents. The protocol was available for both electron-rich and electron-deficient substrates. The ortho-sulfonylated phenol was synthesized expediently from the sulfonylation product by the removal of the pyridyl group. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Synthetic Route of C11H9NO).

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. 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. Synthetic Route of C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Studies on ketene and its derivatives. CXIII. Reaction of dichloroketene with aromatic amine N-oxides was written by Katagiri, Nobuya;Niwa, Ryuji;Furuya, Yoichi;Kato, Tetsuzo. And the article was included in Chemical & Pharmaceutical Bulletin in 1983.SDS of cas: 3718-65-8 This article mentions the following:

Treating pyridine 1-oxide (I) with Cl₂C:C:O gave 4 products, pyridines II (R = H, R¹ = CHCl₂; R = CHCl₂, R¹ = H; R² = H) and furopyridines III (R³ = OH, Cl). Reaction of Cl₂C:C:O with I, followed by treatment with MeOH, gave II (R = CHCl₂, CCl₂CO₂Me, R¹ = H; R = H, R¹ = CCl₂CO₂Me; R² = H). Similar reaction of Cl₂C:C:O with methylpyridine 1-oxides gave the corresponding 2-dichloromethyl- and 4-dichloromethylpyridines. However, reaction of Cl₂C:C:O with 2,6-dimethylpyridine 1-oxide, followed by treatment with MeOH gave II (R = CHCl₂; R¹ = R² = Me) and bis(pyridyl)dichloromethane IV. Cl₂C:C:O reacted with quinoline 1-oxide and isoquinoline 2-oxide to give the corresponding Cl₂CH derivatives In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8SDS of cas: 3718-65-8).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of âˆ?8.7 × 10âˆ? cm3·molâˆ?.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·molâˆ? in the liquid phase and 140.4 kJ·molâˆ? in the gas phase. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.SDS of cas: 3718-65-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

An Efficient Method for the Synthesis of Alkylidenecyclobutanones by Gold-Catalyzed Oxidative Ring Enlargement of Vinylidenecyclopropanes was written by Yuan, Wei;Dong, Xiang;Wei, Yin;Shi, Min. And the article was included in Chemistry – A European Journal in 2012.Electric Literature of C7H9NO This article mentions the following:

Alkylidenecyclobutanones, e.g., I, are prepared from vinylidenecyclopropanes, e.g., II, by a gold-catalyzed oxidative ring expansion. (Triphenylphosphine)gold chloride (5 mol%) and silver hexafluoroantimonate (10 mol%) in the presence of 3,5-dibromopyridine N-oxide (2 equiv) effected the transformation. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Electric Literature of C7H9NO).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) 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. 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.Electric Literature of C7H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Palladium-Catalyzed Electrochemical C-H Alkylation of Arenes was written by Yang, Qi-Liang;Li, Chuan-Zeng;Zhang, Liang-Wei;Li, Yu-Yan;Tong, Xiaofeng;Wu, Xin-Yan;Mei, Tian-Sheng. And the article was included in Organometallics in 2019.Synthetic Route of C12H11N This article mentions the following:

2-Arylpyridines were electrochem. ortho-alkylated by RBF₃K, the reaction being performed in undivided cell in aqueous solutions catalyzed by Pd(OAc)₂. Palladium-catalyzed electrochem. C-H functionalization reactions have emerged as attractive tools for organic synthesis. This process offers an alternative to conventional methods that require harsh chem. oxidants. However, this electrolysis requires divided cells to avoid catalyst deactivation by cathodic reduction Herein, we report the first example of palladium-catalyzed electrochem. C-H alkylation of arenes using undivided electrochem. cells in water, thereby providing a practical solution for the introduction of alkyl group into arenes. 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. 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.Synthetic Route of C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem