Day: February 9, 2023

Scope and limitations of the synthesis of functionalized quinolizidinones and related compounds by a simple precursor approach via addition of lithium allylmagnesates to 2-pyridones and RCM as key steps was written by Sosnicki, Jacek G.;Struk, Lukasz;Idzik, Tomasz;Maciejewska, Gabriela. And the article was included in Tetrahedron in 2014.Name: 5-Phenylpyridin-2-ol This article mentions the following:

The scope and limitations of the simple synthesis of functionalized quinolizidin-4-ones, e.g. I, by chemoselective N-alkenylation of NH pyridin-2(1H)-ones (2-pyridones), regioselective addition of lithium allyl(di-n-butyl)magnesates(1-) to N-alkenylpyridin-2(1H)-ones, followed by ring closing metathesis (RCM) is described. A number of functionalizations introduced into quinolizidin-4-one rings demonstrated the high prospect of the strategy proposed in scaffold synthesis. Their extension to the syntheses of pyrido[1,2-a]azepin-4-one and pyrido[1,2-a]azocin-4-one derivatives as well as to spiro-fused compounds is also presented. In the experiment, the researchers used many compounds, for example, 5-Phenylpyridin-2-ol (cas: 76053-45-7Name: 5-Phenylpyridin-2-ol).

5-Phenylpyridin-2-ol (cas: 76053-45-7) 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. 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.Name: 5-Phenylpyridin-2-ol

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.Synthetic Route of C12H11N 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-(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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Synthetic Route of C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Enantioselective Heck Arylations of Acyclic Alkenyl Alcohols Using a Redox-Relay Strategy was written by Werner, Erik W.;Mei, Tian-Sheng;Burckle, Alexander J.;Sigman, Matthew S.. And the article was included in Science (Washington, DC, United States) in 2012.Category: pyridine-derivatives This article mentions the following:

Nonracemic β-, γ-, and δ-aryl ketones such as (S)-4-MeO₂CC₆H₄CHMeCH₂COMe were prepared in 52-85% yields, 90:10-99:1 er, and with high regioselectivities by Heck reactions of phenyldiazonium tetrafluoroborate or aryldiazonium hexafluorophosphates (generated from the corresponding arylamines) with acyclic allylic, homoallylic, or bishomoallylic alcs. such as (E)-MeCH(OH)CH:CHMe in the presence of tris(dibenzylideneacetone)dipalladium [Pd₂(dba)₃] and the nonracemic trifluoropyridinyl oxazolidine I. I and Pd₂(dba)₃ imparted notable regioselectivity during migratory insertion and promoted migration of alkene unsaturation toward the alc. to form ketones or aldehydes. (E)- and (Z)-allylic and homoallylic alcs. underwent stereospecific Heck reactions to give enantiomeric products; the alc. stereochem. in the racemic unsaturated alcs. did not affect the enantioselectivities of their reactions. The aryldiazonium salts used as reactant can be explosive and should be handled with caution. In the experiment, the researchers used many compounds, for example, (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole (cas: 1257527-14-2Category: pyridine-derivatives).

(S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole (cas: 1257527-14-2) 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 derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Three POM-based coordination polymers: hydrothermal synthesis, characterization, and catalytic activity in epoxidation of styrene was written by Ren, Yuanhang;Du, Chengbo;Feng, Sujiao;Wang, Chunling;Kong, Zuping;Yue, Bin;He, Heyong. And the article was included in CrystEngComm in 2011.Formula: C12H8N4O This article mentions the following:

Three polyoxometalates (POM)-based coordination polymers, [Cu^II₂(C₅H₅NCOO)₂(4-bpo)₂(H₂O)₂]SiW₁₂O₄₀·H₂O (1), [Cu^I₄(4-bpo)₆]SiW₁₂O₄₀·3H₂O (2), and [Cu^I₄(3-bpo)₄]SiW₁₂O₄₀·3H₂O (3), were hydrothermally synthesized from the mixture of H₄SiW₁₂O₄₀, copper salts, and 3-bpo (2,5-bis(3-pyridyl)-1,3,4-oxadiazole) or 4-bpo (2,5-bis(4-pyridyl)-1,3,4-oxadiazole) and characterized by elemental anal., IR spectroscopy, TGA, and single crystal x-ray diffraction. The 4-bpo mols. are connected into an infinite double-chain in compound 1 as a bidentate ligand. Compound 2 contains large hexagonal prism shaped mol. cages defined by copper ions and 4-bpo mols. which wrap Keggin ions inside. In compound 3 {Cu₂(3-bpo)₂} mol. rings connect with Keggin ions to form a 1D chain. By inspection of the structures, the geometry and the coordination mode of bpo ligands play important roles in the formation of 1-3. The catalytic performance of 1-3 was studied for epoxidation of styrene using tert-Bu hydroperoxide (TBHP) as the oxidant. Compounds 1–3 present promising activity as heterogeneous catalysts while compound 1 exhibits the best yield of styrene epoxide. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Formula: C12H8N4O).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) 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.Formula: C12H8N4O

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Design, synthesis, and biological activity of piperidinediamine derivatives as factor Xa inhibitor was written by Mochizuki, Akiyoshi;Nakamoto, Yumi;Naito, Hiroyuki;Uoto, Kouichi;Ohta, Toshiharu. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Recommanded Product: 85838-94-4 This article mentions the following:

Cyclohexanediamine I [X = X¹ = CH₂] was identified as an orally bioavailable factor Xa inhibitor. Two racemic cis-piperidinediamine analogs I [X = NR, X¹ = CH₂; X = CH₂, X¹ = NR] were investigated. I [X = NR, X¹ = CH₂, R = CO₂CMe₃, H, Ac, SO₂Me, CO₂Et] showed higher fXa inhibitory activity, anticoagulant activity, and aqueous solubility than I [X = CH₂, X¹ = NR] having same substituent. I [X = NR, X¹ = CH₂] having sp2 nitrogen, especially amide and urea derivatives, showed potent anticoagulant activity. I [X = NR, X¹ = CH₂, R = OCH₂OMe, NMe₂] showed high oral activities in rats. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Recommanded Product: 85838-94-4).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Triarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines was written by Rao, Maddali L. N.;Dhanorkar, Ritesh J.. And the article was included in European Journal of Organic Chemistry in 2014.COA of Formula: C11H8BrN This article mentions the following:

Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalyzed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both sym. and unsym. diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalyzed conditions. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-phenylpyridine (cas: 54151-74-5COA of Formula: C11H8BrN).

2-Bromo-4-phenylpyridine (cas: 54151-74-5) 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. 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.COA of Formula: C11H8BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Differentiation of substituent effects from hydrogen bonding and protonation effects in carbon-13 NMR spectra of pyridine N-oxides was written by Szafran, Miroslaw;Brycki, Bogumil;Dega-Szafran, Zofia;Nowak-Wydra, Barbara. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1991.Application of 3718-65-8 This article mentions the following:

Aromatic ¹³C chem. shifts are reported by 4- and 3-substituted pyridine N-oxides in deuteriochloroform, deuterium oxide, perchloric acid (60% in D₂O) and dichloroacetic acid (80% in CDCl₃), and also for O-alkylated derivatives in (CD₃)₂SO and D₂O. The substituent chem. shift data show systematic nonadditivity in comparison with monosubstituted benzenes. Data for the position equation. For this position multiple substituent interactions are responsible for the nonadditive shifts; interactions have both an inductive (polar) and a resonance component. Hydrogen bonding and protonation effectes were differentiated from the substituent effect. The relative ¹³C chem.-shift difference [CΔ₃ – Δ₄)/Δ₃] is a measure of the hydrogen bond and protonation effects and is not subject to substituent effects. 3-(Dimethylamino)pyridine N-oxide is protonated at the dimethylamino group, 4-(dimethylamino)pyridine N-oxide at the oxygen. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Application of 3718-65-8).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) 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 3718-65-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Palladium-Catalyzed Alkylation of sp² and sp³ C-H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C-H Activation Pathways was written by Chen, Xiao;Goodhue, Charles E.;Yu, Jin-Quan. And the article was included in Journal of the American Chemical Society in 2006.COA of Formula: C8H11N This article mentions the following:

Palladium-catalyzed alkylations of sp² and sp³ C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag₂O or Ag₂CO₃ is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alc., and alkene functional groups are tolerated. A new C-H activation pathway differing from the cyclometalation process is elucidated using methylboroxine as the coupling partner. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4COA of Formula: C8H11N).

2-Isopropylpyridine (cas: 644-98-4) 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.COA of Formula: C8H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Luminescent lanthanides complexes with mesogenic pyridone ligands: Emission and liquid crystals properties was written by Chiriac, Laura F.;Ilis, Monica;Circu, Viorel. And the article was included in Polyhedron in 2020.Recommanded Product: 626-64-2 This article mentions the following:

In this work, a systematic investigation of the influence of N-alkylated 4-pyridone ligands containing one cyanobiphenyl mesogenic group linked via a spacer with variable length (6, 8, 9 or 10 methylene groups) on the liquid crystalline properties and luminescence properties of the resulting lanthanide complexes with Eu(III), Sm(III) and Tb(III). The chem. structures of the new products were determined by ¹H and ¹³C NMR spectroscopy, as well as elemental anal. and IR spectroscopy. The lanthanide ions are 9-coordinate and surrounded by three pyridone ligands and three bidentate nitrate ions. The thermal behavior of the new products was analyzed by differential scanning calorimetry (DSC) and thermogravimetrical anal. (TG). The nature of the liquid crystalline phase was confirmed by polarizing optical microscopy (POM) and powder x-ray diffraction (XRD) studies. All complexes remain in the glassy state at room temperature while at higher temperature these materials display a SmA phase. Higher clearing temperatures were recorded for longer spacers. The emission spectra show characteristic emission bands for each lanthanide ion. The emission of the new complexes measured as a function of temperature decreases noticeably upon the increase of temperature and this process is reversible on cooling. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Recommanded Product: 626-64-2).

Pyridin-4-ol (cas: 626-64-2) 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.Recommanded Product: 626-64-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Discovery of 9,10-dihydrophenanthrene derivatives as SARS-CoV-2 3CL^pro inhibitors for treating COVID-19 was written by Zhang, Jian-Wei;Xiong, Yuan;Wang, Feng;Zhang, Fu-Mao;Yang, Xiaodi;Lin, Guo-Qiang;Tian, Ping;Ge, Guangbo;Gao, Dingding. And the article was included in European Journal of Medicinal Chemistry in 2022.Electric Literature of C6H6BrNO2S This article mentions the following:

The epidemic coronavirus disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has now spread worldwide and efficacious therapeutics are urgently needed. 3-Chymotrypsin-like cysteine protease (3CL^pro) is an indispensable protein in viral replication and represents an attractive drug target for fighting COVID-19. Herein, we report the discovery of 9,10-dihydrophenanthrene derivatives as non-peptidomimetic and non-covalent inhibitors of the SARS-CoV-2 3CL^pro. The structure-activity relationships of 9,10-dihydrophenanthrenes as SARS-CoV-2 3CL^pro inhibitors have carefully been investigated and discussed in this study. Among all tested 9,10-dihydrophenanthrene derivatives, C1 and C2 display the most potent SARS-CoV-2 3CL^pro inhibition activity, with IC₅₀ values of 1.55 ± 0.21μM and 1.81 ± 0.17μM, resp. Further enzyme kinetics assays show that these two compounds dose-dependently inhibit SARS-CoV-2 3CL^provia a mixed-inhibition manner. Mol. docking simulations reveal the binding modes of C1 in the dimer interface and substrate-binding pocket of the target. In addition, C1 shows outstanding metabolic stability in the gastrointestinal tract, human plasma, and human liver microsome, suggesting that this agent has the potential to be developed as an orally administered SARS-CoV-2 3CL^pro inhibitor. In the experiment, the researchers used many compounds, for example, 2-Bromo-5-(methylsulfonyl)pyridine (cas: 343262-51-1Electric Literature of C6H6BrNO2S).

2-Bromo-5-(methylsulfonyl)pyridine (cas: 343262-51-1) 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. 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.Electric Literature of C6H6BrNO2S

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem