Day: January 30, 2023

Cross-Coupling Reactions through the Intramolecular Activation of Alkyl(triorgano)silanes was written by Nakao, Yoshiaki;Takeda, Masahide;Matsumoto, Takuya;Hiyama, Tamejiro. And the article was included in Angewandte Chemie, International Edition in 2010.Reference of 644-98-4 This article mentions the following:

Cross-coupling reactions of 2-(2-hydroxyprop-2-yl)phenyl-substituted alkylsilanes, e.g., I, with a variety of aryl bromides/chlorides, e.g., 4-chlorobenzonitrile, proceeded in the presence of palladium and copper catalysts to give alkyl-coupled products, e.g., 4-butylbenzonitrile. The use of K₃PO₄ allowed for highly chemoselective alkyl coupling with both primary and secondary alkyl groups. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Reference of 644-98-4).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Research progress in degradation of ionic liquids was written by Dong, Shijia;Zhang, Bixian;Gao, Yunfei;Hu, Xiaomei. And the article was included in Huagong Jinzhan in 2015.Application In Synthesis of 1-Butyl-3-methylpyridinium Chloride This article mentions the following:

A review, with 41 references, is given on the research progress in degradation of ionic liquids As”green solvents”, ionic liquids have attracted much attention in the area of electrochem., organic chem. and biochem. Recent studies focus on the synthesis and application of ionic liquids However, the studies on degradation of ionic liquids which concerned with environment are not enough. The degradation of ionic liquids is required before the large-scale use of ionic liquids In this study, chem. degradation method and biodegradation method are summarized. The chem. degradation is mainly achieved by UV/H₂O₂, Fe(III)/H₂O₂ and electrolysis system. Biol. degradation is achieved by introducing functional groups with enzymic site, or using monooxygenase to oxidize the Me terminal of alkyl side chain on the cation of ionic liquids into hydroxyl and aldehyde to form carboxylic groups, and then β-oxidation is carried out. Different chem. structures of ionic liquids are designed according to different mechanism between chem. and biol. degradation, for example, changing the length of alkyl chain or introducing the functional groups that are easily degradable and selection of microorganism could improve efficiency of degradation of ionic liquids In the experiment, the researchers used many compounds, for example, 1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3Application In Synthesis of 1-Butyl-3-methylpyridinium Chloride).

1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3) 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. 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.Application In Synthesis of 1-Butyl-3-methylpyridinium Chloride

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis, Crystal Structure, and Antibacterial Activity of 1,2,4-Triazoles and 1,2,4-Triazol-3-one was written by Ben Salah, Bochra;Chaari, Najla;Rekik, Awatef;Ben Hsouna, Anis;Trigui, Mohamed;Kossentini, Mohamed. And the article was included in Journal of Heterocyclic Chemistry in 2015.Electric Literature of C5H6ClN This article mentions the following:

A straightforward method has been developed for the synthesis of 1,2,4-triazol-3-one 3 and 1,2,4-triazoles 6a, 6b, 6c, 6d starting from N¹-substituted-N¹-tosylhydrazonates 2 and hydrazine monohydrate. This methodol. affords a number of 1,2,4-triazol-3-one 3 and 1,2,4-triazoles 6a, 6b, 6c, 6d in reasonable yields. The structures of all new compounds were elucidated using IR, ¹H and ¹³C NMR, high-resolution mass spectrometry, elemental anal., and the X-ray crystallog. (for compounds 3 and 6a). Some of the newly synthesized compounds were screened for their antibacterial activity. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Electric Literature of 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. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Electric Literature of C5H6ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Selective CO₂ adsorption and Lewis acid catalytic activity towards naphthimidazole synthesis by a Zn-MOF was written by Agarwal, Rashmi A.;De, Dinesh. And the article was included in Polyhedron in 2020.Application In Synthesis of Pyridin-4-ol This article mentions the following:

A two-fold interpenetrated, three dimensional Zn-based porous MOF, {[Zn(BPBA)Cl]·5H₂O}_n (1) [BPBA = 3,5-bis-(4-oxo-4H-pyridin-1-yl)-benzoate], has been synthesized at high temperature under solvothermal conditions by the in situ acidic hydrolysis of the tripodal ligand 3,5-bis-(4-oxo-4H-pyridin-1-yl)-benzonitrile (BPBN). The de-solvated MOF exhibited selective CO₂ adsorption at 195 K and 1 bar pressure over N₂ and H₂. Interestingly, the four coordinated Zn(II) sites in the MOF exhibited high Lewis acidic heterogeneous catalytic activity for the synthesis of naphthimidazole in excellent yield without pre-activation of the MOF. The Zn(II) sites could directly coordinate to the substrate to catalyze the chem. transformation by an expansion of the coordination number The π-π supramol. interactions between the aromatic rings of the framework and the substrate mol. might help in the substrate activation. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Application In Synthesis of Pyridin-4-ol).

Pyridin-4-ol (cas: 626-64-2) 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.Application In Synthesis of Pyridin-4-ol

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Discovery of isoquinolinone and naphthyridinone-based inhibitors of poly(ADP-ribose) polymerase-1 (PARP1) as anticancer agents: Structure activity relationship and preclinical characterization was written by Karche, Navnath P.;Bhonde, Mandar;Sinha, Neelima;Jana, Gourhari;Kukreja, Gagan;Kurhade, Sanjay P.;Jagdale, Arun R.;Tilekar, Ajay R.;Hajare, Anil K.;Jadhav, Ganesh R.;Gupta, Nishant R.;Limaye, Rohan;Khedkar, Nilesh;Thube, Baban R.;Shaikh, Javed S.;Rao Irlapati, Nageswara;Phukan, Samiron;Gole, Gopal;Bommakanti, Apparao;Khanwalkar, Harshal;Pawar, Yogesh;Kale, Ramesh;Kumar, Rakesh;Gupta, Rajesh;Praveen Kumar, V. R.;Wahid, Saif;Francis, Albi;Bhat, Tariq;Kamble, Nivrutti;Patil, Vinod;Nigade, Prashant B.;Modi, Dipak;Pawar, Shashikant;Naidu, Sneha;Volam, Harish;Pagdala, Vamsi;Mallurwar, Sadanand;Goyal, Hemant;Bora, Pushpak;Ahirrao, Prajakta;Singh, Minakshi;Kamalakannan, Prabhakaran;Naik, Kumar Ram;Kumar, Pradipta;Powar, Rajendra G.;Shankar, Rajesh B.;Bernstein, Peter R.;Gundu, Jayasagar;Nemmani, Kumar;Narasimham, Lakshmi;George, Kochumalayil Shaji;Sharma, Sharad;Bakhle, Dhananjay;Kamboj, Rajender Kumar;Palle, Venkata P.. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Recommanded Product: 3939-12-6 This article mentions the following:

The exploitation of GLU988 and LYS903 residues in PARP1 as targets to design isoquinolinone and naphthyridinone analogs is described. Compounds of structure I have good biochem. and cellular potency but suffered from inferior PK. Constraining the linear propylene linker of structure into a cyclopentene ring offered improved PK parameters, while maintaining potency for PARP1. Finally, to avoid potential issues that may arise from the presence of an anilinic moiety, the nitrogen substituent on the isoquinolinone ring was incorporated as part of the bicyclic ring. This afforded a naphthyridinone scaffold, as shown in structure naphthyridinones. Further optimization of naphthyridinone series led to identification of a novel and highly potent PARP1 inhibitor I, which was further characterized as preclin. candidate mol. Compound I is orally bioavailable and displayed favorable pharmacokinetic (PK) properties. Compound I demonstrated remarkable antitumor efficacy both as a single-agent as well as in combination with chemotherapeutic agents in the BRCA1 mutant MDA-MB-436 breast cancer xenograft model. Addnl., compound I also potentiated the effect of agents such as temozolomide in breast cancer, pancreatic cancer and Ewing’s sarcoma models. In the experiment, the researchers used many compounds, for example, 6-Fluoronicotinonitrile (cas: 3939-12-6Recommanded Product: 3939-12-6).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and Characterization of a Series of Bis-homoleptic Cycloruthenates with Terdentate Ligands as a Family of Panchromatic Dyes was written by Rees, Thomas W.;Liao, Jin Feng;Sinopoli, Alessandro;Male, Louise;Calogero, Giuseppe;Curchod, Basile F. E.;Baranoff, Etienne. And the article was included in Inorganic Chemistry in 2017.Computed Properties of C8H8BrNO2 This article mentions the following:

Six homoleptic bis-cyclometalated ruthenium complexes, Ru(NN̂Ĉ)₂, is reported where NN̂Ĉ is a 6-(2,4-difluoro-3-R³-phenyl)-4-R²-4′-R¹-2,2′-bipyridine with R³ = -H or -CF₃ and R² and R¹ = -COOEt or -CF₃. An effective synthesis of the ligands and the complexes is described. The UV-visible absorption studies demonstrate that these complexes are panchromatic dyes absorbing up to 900 nm. Importantly, the onset of absorption depends only on the substitution on the metalated Ph, whereas the intensity of absorption throughout the spectra is a function of substituents on both the Ph and the bipyridine moieties. The same trend is observed in electrochem. as the redox gap depends only on the substitution on the metalated Ph, whereas the oxidation and reduction potentials are a function of substituents on both the Ph and the bipyridine moieties. Preliminary tests as sensitizer for dye-sensitized solar cells demonstrate that the number of anchoring groups on the dye has a major influence on the device efficiency. In the experiment, the researchers used many compounds, for example, Ethyl 2-bromoisonicotinate (cas: 89978-52-9Computed Properties of C8H8BrNO2).

Ethyl 2-bromoisonicotinate (cas: 89978-52-9) 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. 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.Computed Properties of C8H8BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rapid and Efficient Construction of Indolizino[3,4,5-ab]isoindole Skeletons by a Rhodium-Catalyzed Tandem Reaction was written by Liu, Chang;Wu, Shaonan;Sun, Wan;Meng, Haifang;Xing, Siyang;Zhu, Bolin. And the article was included in Asian Journal of Organic Chemistry in 2020.Formula: C12H11N This article mentions the following:

A facile rhodium-catalyzed tandem reaction of two mols. of acrylates with two mols. of 2-phenylpyridines involving sequential C-H activation, Michael addition, [12+2] cycloaddition and oxidative aromatization was described. A series of indolizino[3,4,5-ab]isoindole compounds were efficiently afforded in good yields by the formation of two C-C bonds, two C=C bonds and one C-N bond. 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. 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 groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Formula: C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Condensation of substituted 2-aminopyridine with β-keto carboxylic esters: 4H-pyrido[1,2-a]pyrimidin-4-ones and pyridin-2-ones was written by Ferrarini, Pier Luigi;Mori, Claudio;Manera, Clementina;Mori, Filippo;Calderone, Vincenzo;Martinotti, Enrica. And the article was included in Journal of Heterocyclic Chemistry in 1999.Synthetic Route of C7H9N3O This article mentions the following:

The condensation of substituted 2-aminopyridines 5 with β-keto carboxylic esters in polyphosphoric acid is reported. In addition to the target compounds, 4H-pyrido[1,2-a]pyrimidin-4-ones, 1-(2-pyridinyl)-2-pyridinones were also obtained in this reaction. The latter compounds were tested for their Ca-antagonistic activity but failed to evoke any vasorelaxant response. In the experiment, the researchers used many compounds, for example, N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3Synthetic Route of C7H9N3O).

N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3) 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.Synthetic Route of C7H9N3O

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Derivatives of pyridine and quinoline. LXXXVII. Bromo derivatives of 3-hydroxypyridine was written by den Hertog, H. J.;Schepman, F. R.;de Bruyn, J.;Thysse, G. J. E.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas in 1950.Safety of 2,6-Dibromo-3-hydroxypyridine This article mentions the following:

The preparation of 8 Br derivatives of 3-hydroxypyridine is described: 2-Br, m. 186.5-7°, from 2-nitro-3-ethoxypyridine as given previously (C.A. 43, 6625h) with HBr in HOAc; 4-Br, m. 123.5-4° (20% from 0.5 g. 3,4-dihydroxypyridine and 4 g. POBr₃ at 130° for 4 hrs.; 5-Br, m. 166.5-7.5°, from 1.4 g. 5-bromo-3 ethoxypyridine heated 4 hrs. at 160-70° in 25 ml. aqueous 25% HCl; 6-Br, m. 135.5-6.5° (90-100% from 0.16 g. 6-bromo-3-ethoxypyridine heated in 40% of HBr 8 hrs. at 160°); 2,6-di-Br, m. 162-3°, from 0.5 g. 2-bromo-3-ethoxy-6-nitropyridine heated to 130° for 4 hrs. with 5 ml. of 40% HBr; 4,6(possibly 2,4)-di-Br, m. 190-1°, from 1 g. 2,4,6-tribromo-3-hydroxypyridine boiled 4-5 hrs. with 1.5 g. N₂H₄.H₂O in 8 ml. EtOH; 2,4,6-tri-Br (I), m. 90.5-91° (50% by brominating 0.5 g. 3-hydroxypyridine in aqueous Br to discoloration). A similar product is obtained by brominating either 2-bromo-3-hydroxypyridine (45% yield, m. 86-7°) or 6-bromo-3-hydroxypyridine (65-70% yield, m. 85-8°). I (1 g.) treated with 0.8 g. NaOH in 18 ml. MeOH at 140° for 5 hrs. gives 2-methoxy-4,6-dibromo-3-hydroxypyridine, m. 86-7°. Hydrogenation in an alk. EtOH solution yields 2,3-dihydroxypyridine, m. 247-8°. Addition of N₂H₄.H₂O in EtOH to I yields the hydrazinium salt of 2,4-6-tribromo-3-hydroxypyridine, C₅H₂ONBr₃.N₂H₂, m. 179-9.5°. 2,4,5,6-Tetrabromo-3 hydroxypyridine, m. 146.5-7.5°, was prepared by adding 5-bromo-3-hydroxypyridine to aqueous HBr. solution In the experiment, the researchers used many compounds, for example, 2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1Safety of 2,6-Dibromo-3-hydroxypyridine).

2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1) 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.Safety of 2,6-Dibromo-3-hydroxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rhodium-Catalyzed Asymmetric Conjugate Pyridylation with Pyridylboronic Acids was written by Ye, Bihai;Yao, Jian;Wu, Changhui;Zhu, Huilong;Yao, Weijun;Jin, Lili;Dou, Xiaowei. And the article was included in ACS Catalysis in 2022.Computed Properties of C5H4BCl2NO2 This article mentions the following:

In this study, the rhodium-catalyzed asym. conjugate pyridylation of α,β-unsaturated carbonyl compounds with pyridylboronic acids was reported. The bifunctional chiral amide-diene ligand, which dramatically accelerated the reaction via possible H-bonding activation, and alc. solvent, which significantly inhibited the competing protodeboronation of pyridylboronic acids under rhodium catalysis, worked in concert to promote the reaction, thus enabling production of the pyridylation products in high yields (up to 99%) with good enantioselectivities (up to >99% ee). In the experiment, the researchers used many compounds, for example, (2,6-Dichloropyridin-4-yl)boronic acid (cas: 1072951-54-2Computed Properties of C5H4BCl2NO2).

(2,6-Dichloropyridin-4-yl)boronic acid (cas: 1072951-54-2) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Computed Properties of C5H4BCl2NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem