Category: pyridine-derivatives

In 2018,Chen, Long; Zhu, Yueyue; Chen, Tieqiao; Liu, Long; Zhang, Ji-Shu; Han, Li-Biao published 《Direct C-OH/P(O)-H dehydration coupling forming phosphine oxides》.Organic & Biomolecular Chemistry published the findings.Reference of 2-(2-Hydroxyethyl)pyridine The information in the text is summarized as follows:

A t-BuONa-mediated C-OH/P(O)-H cross dehydration coupling to produce alkylphosphine oxides is developed. This reaction employed readily available alcs. and P(O)-H compounds as the starting materials, providing an efficient alternative method for constructing sp3 C-P bonds. A reasonable reaction path involving dehydration and subsequent regio-selective hydrophosphorylation of the resulting alkenes was proposed. In the experimental materials used by the author, we found 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Reference of 2-(2-Hydroxyethyl)pyridine)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Reference of 2-(2-Hydroxyethyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Awwadi, Firas F.; Turnbull, Mark M.; Alwahsh, Manal I.; Haddad, Salim F. published 《May halogen bonding interactions compete with Cu···Cl semi-coordinate bonds? Structural, magnetic and theoretical studies of two polymorphs of trans-bis(5-bromo-2-chloro pyridine)dichlorocopper(II) and trans-bis(2,5-dichloropyridine)dichlorocopper(II)》.New Journal of Chemistry published the findings.Reference of 5-Bromo-2-chloropyridine The information in the text is summarized as follows:

Two polymorphs of Cu(25dcp)2Cl2 [Cu(25dcp)2Cl2_p1 and Cu(25dcp)2Cl2_p2] and Cu(5b2cp)2Cl2 [Cu(5b2cp)2Cl2_p1 and Cu(5b2cp)2Cl2_p2] were prepared and characterized by single crystal X-ray diffraction (25dcp = 2,5-dichloropyridine and 5b2cp = 5-bromo-2-chloropyridine). The four structures crystallize in the monoclinic crystal system: three of them (Cu(25dcp)2Cl2_p1, Cu(5b2cp)2Cl2_p2 and Cu(25dcp)2Cl2_p2) crystallize in the C2/c space group and the fourth one (Cu(5b2cp)2Cl2_p1) in the C2/m space group. Cu(5b2cp)2Cl2_p1 and Cu(25dcp)2Cl2_p1 are structurally isomorphous. The formation of two polymorphs for each complex is a result of competition between Cl···Cu semi-coordinate bonds and C-X···Cl-Cu (X = Cl or Br) halogen bonding interactions. The formation of C-X···Cl-Cu halogen bonding alone resulted in crystallization of Cu(25dcp)2Cl2_p1 and Cu(5b2cp)2Cl2_p1, whereas the formation of the Cu···Cl semi-coordinate bonds resulted in the formation of Cu(25dcp)2Cl2_p2 and Cu(5b2cp)2Cl2_p2. To our knowledge, these are the first examples in which the competition between the halogen bonding interactions and the semi-coordinate Cu···Cl resulted in the formation of different polymorphs. The calculated electrostatic potential was used to rationalize the formation of the different polymorphs. The magnetic properties of Cu(5b2cp)2Cl2_p1 were studied; it is found to obey an antiferromagnetic chain model. This magnetic behavior was rationalized using the two-halide exchange pathway. Structurally, Cu(5b2cp)2Cl2_p1 forms a chain structure based on Cu-Cl···Cl-Cu interactions. The mapped electron d. with spin d. showed the presence of a spin-d.-end-cap along the Cu-Cl bond. This spin-d.-end-cap corroborates the observed antiferromagnetic interactions. In the experiment, the researchers used 5-Bromo-2-chloropyridine(cas: 53939-30-3Reference of 5-Bromo-2-chloropyridine)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Reference of 5-Bromo-2-chloropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Yao, Qiyi; Kong, Lingkai; Zhang, Fangfang; Tao, Xianghua; Li, Yanzhong published 《Base-Promoted Tandem Reaction towards Conjugated Dienone or Chromone Derivatives with a Cyano Group: Insertion of Alkynes into C-C σ-Bonds of 3-Oxopropanenitriles》.Advanced Synthesis & Catalysis published the findings.Application of 128071-75-0 The information in the text is summarized as follows:

Base-promoted insertion reactions of alkynes into the C-C σ-bonds of α-cyano ketones were established to construct highly functionalized conjugated olefins I [R1 = cyclohexyl, Ph, 4-BrC6H4, 3,4,5-(MeO)3C6H2, etc.; R2 = Ph, 4-ClC6h4, 4-MeC6H4, 4-MeOC6H4; R3 = Ph] or chromone derivatives II [X = CH, N; R3 = t-Bu, Ph; R4 = H, 6-F, 7-F, 6,7-(MeO)2; R5 = Me, n-Bu, Ph, 3,4,5-(MeO)3C6H2, 2-naphthyl, etc.] via transition metal-free tandem reactions. Nucleophilic attack of α-cyano ketones R3C(O)CH2CN to alkynones R1C(O)CCR2 followed by intramol. nucleophilic addition/ring-opening furnished the cyano-containing alkenes I. In the cases of alkynones III (Z = Br, Cl, F) bearing an ortho-halide-substituted aryl ring, a further C-O bond coupling reaction occurred to afford chromone derivatives II in good to high yields. Various alkynones bearing alkyl or aryl substituents were compatible in the reaction. This reaction has the potential to become a general synthetic protocol for the preparation of cyano-substituted olefins and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups. In the part of experimental materials, we found many familiar compounds, such as 2-Bromonicotinaldehyde(cas: 128071-75-0Application of 128071-75-0)

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Application of 128071-75-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Zhang, Wen-Man; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian published 《Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides》.Journal of Organic Chemistry published the findings.Related Products of 103-74-2 The information in the text is summarized as follows:

A photoredox catalytic method has been developed for the direct C2 alkylation of pyridine N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2-alkylated pyridine N-oxides under mild conditions. Mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway. The experimental process involved the reaction of 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Related Products of 103-74-2)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Related Products of 103-74-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2016,Ibrahim, Halliru; Bala, Muhammad Dabai published 《Earth abundant metal complexes of donor functionalised N-heterocyclic carbene ligands: synthesis, characterisation and application as amination catalysts》.New Journal of Chemistry published the findings.Computed Properties of C6H7Br2N The information in the text is summarized as follows:

Six new imidazolium salts of the form 3-R-1-picolylimidazolium bromide (1a: R = 4-nitrophenyl, 1b: R = 4-acetylphenyl, 1c: R = 4-cyanophenyl, 1d: R = allyl, 1e: R = butenyl, 1f: R = pentenyl) were synthesized and isolated in high yields. The corresponding Ag-NHC intermediate complexes 2a, 2d, and 2e were transmetalated to yield [M(NHC)2Cl2 M = Co, Ni] complexes in good to excellent yields. The Co-NHC (3a, 3d, 3e) and Ni-NHC (3a’, 3d’, 3e’) complexes were relatively stable in air, insoluble in chlorinated solvents but very soluble in methanol and DMSO. Poorly resolved NMR spectra and magnetic susceptibility values of 2.53 and 2.73 μB for 3d and 3e resp. suggest both to be paramagnetic cobalt complexes. All the imidazolium salts, isolated Ag-NHC complexes and the corresponding Co and Ni-NHC complexes were characterized by spectroscopic and anal. techniques. The complexes are active at low catalyst loading (1 mol%) for the C-N coupling of aniline with Ph bromide under mild reaction conditions. The in situ generated catalyst obtained from a mixture of NiCl2/1a (1:2 molar ratio) initiated the C-N coupling of several aryl amines with substituted aryl bromides bearing a wide variety of functional groups. Good to excellent yields of the desired diaryl amine products were obtained. The yields are comparable to data obtained with palladium catalysts or to data obtained under harsher temperature conditions of Cu mediated Ullman reactions. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Computed Properties of C6H7Br2N)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Computed Properties of C6H7Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2014,Perato, Serge; De Giorgi, Marcella; Burzicki, Gregory; Legalite, Florent; Rault, Sylvain; Voisin-Chiret, Anne Sophie published 《Focus on microwave assisted halogen-halogen exchange reaction conditions on 2-halopyridines》.Current Microwave Chemistry published the findings.Category: pyridine-derivatives The information in the text is summarized as follows:

This paper describes an optimized microwave irradiation-assisted methodol. for halogen-halogen exchange reactions on various substituted pyridines. The protocol provides an efficient and simple methodol. to improve the reactivity of some positions on the pyridine ring towards metallocatalyzed reactions. Influence of various substituents were explored and limiting factors of reaction highlighted. In addition to this study using 5-Bromo-2-chloropyridine, there are many other studies that have used 5-Bromo-2-chloropyridine(cas: 53939-30-3Category: pyridine-derivatives) was used in this study.

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Carpenter, Joseph; Wu, Gang; Wang, Ying; Cook, Erica M.; Wang, Tao; Sitkoff, Doree; Rossi, Karen A.; Mosure, Kathy; Zhuo, Xiaoliang; Cao, Gary G.; Ziegler, Milinda; Azzara, Anthony V.; Krupinski, Jack; Soars, Matthew G.; Ellsworth, Bruce Alan; Wacker, Dean A. published 《Discovery of BMS-986318, a Potent Nonbile Acid FXR Agonist for the Treatment of Nonalcoholic Steatohepatitis》.ACS Medicinal Chemistry Letters published the findings.Related Products of 29682-15-3 The information in the text is summarized as follows:

Herein we report the discovery and preclin. biol. evaluation of 6-(2-(5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)isoxazol-4-yl)-7-azaspiro[3.5]non-1-en-7-yl)-4-(trifluoromethyl)quinoline-2-carboxylic acid, compound 1 (BMS-986318), a nonbile acid farnesoid X receptor (FXR) agonist. Compound 1 exhibits potent in vitro and in vivo activation of FXR, has a suitable ADME profile, and demonstrates efficacy in the mouse bile duct ligation model of liver cholestasis and fibrosis. The overall profile of compound 1 supports its continued evaluation. In the experiment, the researchers used Methyl 5-bromopicolinate(cas: 29682-15-3Related Products of 29682-15-3)

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. When pyridine is adsorbed on oxide surfaces or in porous materials, the following species are commonly observed: (i) pyridine coordinated to Lewis acid sites, (ii) pyridine H-bonded to weakly acidic hydroxyls, and (iii) protonated pyridine. At high coverage, physisorbed pyridine and protonated dimers can also be observed.Related Products of 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zheng, Yi; Obeng, Samuel; Wang, Huiqun; Jali, Abdulmajeed M.; Peddibhotla, Bharath; Williams, Dwight A.; Zou, Chuanchun; Stevens, David L.; Dewey, William L.; Akbarali, Hamid I.; Selley, Dana E.; Zhang, Yan published an article on January 24 ,2019. The article was titled 《Design, Synthesis, and Biological Evaluation of the Third Generation 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido]morphinan (NAP) Derivatives as μ/κ Opioid Receptor Dual Selective Ligands》, and you may find the article in Journal of Medicinal Chemistry.Recommanded Product: 59290-82-3 The information in the text is summarized as follows:

μ Opioid receptor (MOR) agonists have been widely applied for treating moderate to severe pain. However, numerous adverse effects have been associated with their application, including opioid-induced constipation (OIC), respiratory depression, and addiction. On the basis of previous work in our laboratory, NAP, a 6β-N-4′-pyridyl substituted naltrexamine derivative, was identified as a peripheral MOR antagonist that may be used to treat OIC. To further explore its structure-activity relationship, a new series of NAP derivatives were designed, synthesized, and biol. evaluated. Among these derivatives, NFP and NYP significantly antagonized the antinociception effect of morphine. Whereas NAP acted mainly peripherally, its derivatives NFP and NYP actually can act centrally. Furthermore, NFP produced significantly lesser withdrawal symptoms than naloxone at similar doses. These results suggest that NFP has the potential to be a lead compound to treat opioid abuse and addiction. The experimental part of the paper was very detailed, including the reaction process of 3-Nitroisonicotinic acid(cas: 59290-82-3Recommanded Product: 59290-82-3)

3-Nitroisonicotinic acid(cas: 59290-82-3) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Recommanded Product: 59290-82-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Ju, Zhao-Yang; Song, Li-Na; Chong, Ming-Ben; Cheng, Dang-Guo; Hou, Yang; Zhang, Xi-Ming; Zhang, Qing-Hua; Ren, Lan-Hui published an article in Journal of Organic Chemistry. The title of the article was 《Selective Aerobic Oxidation of Csp3-H Bonds Catalyzed by Yeast-Derived Nitrogen, Phosphorus, and Oxygen Codoped Carbon Materials》.COA of Formula: C7H7NO The author mentioned the following in the article:

Nitrogen, phosphorus and oxygen codoped carbon catalysts were successfully synthesized using dried yeast powder as pyrolysis precursor. The yeast-derived heteroatom-doped carbon (yeast@C) catalysts exhibited outstanding performance in the oxidation of Csp3-H bonds to ketones and esters giving excellent products yields (up to 98% yield) without organic solvents at low O2 pressure (0.1 MPa). The catalytic oxidation protocol exhibited broad range of substrates (38 examples) with good functional group tolerance, excellent regioselectivity and synthetic utility. The yeast-derived heteroatom-doped carbon catalysts showed good reusability and stability after recycle six times without any significant loss of activity. Exptl. results and DFT calculations proved the important role of N-oxide (N+-O-) on the surface of yeast@C and a reasonable carbon radical mechanism. In the experiment, the researchers used 4-Acetylpyridine(cas: 1122-54-9COA of Formula: C7H7NO)

4-Acetylpyridine(cas: 1122-54-9) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.COA of Formula: C7H7NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Zhang, Zhen; Li, Jie; Chen, Hao; Huang, Jing; Song, Xiaojuan; Tu, Zheng-Chao; Zhang, Zhang; Peng, Lijie; Zhou, Yang; Ding, Ke published an article in Journal of Medicinal Chemistry. The title of the article was 《Design, Synthesis, and Biological Evaluation of 2-Formyl Tetrahydronaphthyridine Urea Derivatives as New Selective Covalently Reversible FGFR4 Inhibitors》.Reference of 4-Ethynylpyridine The author mentioned the following in the article:

Aberrant FGF19/FGFR4 signaling is an oncogenic driver force for the development of human hepatocellular carcinoma (HCC). A series of 2-formyl tetrahydronaphthyridine urea derivatives I (R = 2-phenylethynyl, 2-(pyridin-2-yl)ethynyl, 2-(3-methoxyphenyl)ethyl, etc.; R1 = F, propan-2-yloxidanyl, cyclopentylaminyl, etc.) and II was designed and synthesized as new covalently reversible inhibitors of FGFR4. The representative compound II (R = 2-(pyridin-3-yl)ethynyl) (III) exhibited an IC50 value of 5.4 nM against FGFR4 and demonstrated extraordinary kinome selectivity. Compound III also exhibited good oral pharmacokinetic properties with an AUC(0-t) value of 38 950.06 h*ng/mL, a T1/2 value of 3.06 h, and an oral bioavailability of 50.97%, at an oral dose of 25 mg/kg in Sprague-Dawley (SD) rats. Furthermore, compound III induced significant tumor regressions in a xenograft mouse model of Hep3B2.1-7 HCC cancer cells without an obvious sign of toxicity upon 30 mg/kg oral administration. Compound III may serve as a promising lead compound for further anticancer drug development. After reading the article, we found that the author used 4-Ethynylpyridine(cas: 2510-22-7Reference of 4-Ethynylpyridine)

4-Ethynylpyridine(cas: 2510-22-7) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Reference of 4-Ethynylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem