Tag: 200-300

Copper-Catalyzed N-Arylation of 2-Pyridones Employing Diaryliodonium Salts at Room Temperature was written by Jung, Seo-Hee;Sung, Dan-Bi;Park, Cho-Hee;Kim, Won-Suk. And the article was included in Journal of Organic Chemistry in 2016.Name: 3,5-Dibromo-2-hydroxypyridine This article mentions the following:

A new and mild synthetic approach for the N-arylation of 2-pyridones with diaryliodonium salts has been developed. Most reactions proceed readily at room temperature in the presence of 10 mol % of copper chloride. As a result, a wide range of N-arylpyridine-2-ones were synthesized in yields of 23% to 99%. With this method, an antifibrotic drug, Pirfenidone, was successfully synthesized in 99% yield within 30 min at room temperature In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6Name: 3,5-Dibromo-2-hydroxypyridine).

3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6) 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. 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.Name: 3,5-Dibromo-2-hydroxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Copper (I) coordination polymers with extended π···π interactions: syntheses, structures, characterization and luminescent properties was written by Huang, Ting-hong;Yan, Jie;Yang, Hu;Zeng, Xian-guang;Yang, Yan. And the article was included in Wuji Huaxue Xuebao in 2015.Synthetic Route of C12H8N4O This article mentions the following:

Two copper(I) coordination polymers, {[Cu₂(4-bpo)₂(MeCN)₂(PPh₃)₂](BF₄)₂}_n (1), {[Cu(4-bpo)(MeCN)(dppe)_0.5]BF₄}_n (2) (PPh₃ = triphenylphosphine, dppe = 1,2-bis(di-Ph phosphino)ethane, 4-bpo = 2,5-bis(4-pyridyl)-1,3,4-oxadiazole), were synthesized and characterized by IR, ¹H NMR, ¹⁹F NMR, ¹¹B NMR, elemental anal. and x-ray crystal structure anal. The structural anal. showed that complexes 1 and 2 consisted of diverse and interesting 2D supramol. structures formed by inter-chain interactions. For 1, π-stacking interactions result in the construction of 1D bilayer chain and 2D supramol. network. Compound 2 exhibits a 1D ladder-like chain and a 1D+1D→2D/3D supramol. structure formed by π-stacking interactions. Solid-state emission spectra of complexes 1 and 2 were studied, displaying the existence of ILCT/MLCT excited states. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Synthetic Route of C12H8N4O).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) 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 groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Synthetic Route of C12H8N4O

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rearrangement of N,N-Di-tert-butoxycarbonylpyridin-4-amines and Formation of Polyfunctional Pyridines was written by Liu, Yahua;Ding, Qiang;Wu, Xu. And the article was included in Journal of Organic Chemistry in 2008.Reference of 209798-48-1 This article mentions the following:

N,N-Di-tert-butoxycarbonylpyridin-4-amines I (R¹ = R² = Cl; R¹ = Cl, Br, tert-Bu, R² = H) were found to be rearranged to tert-Bu 4-(tert-butoxycarbonylamino)nicotinates II by treatment with LDA in THF. In the experiment, the researchers used many compounds, for example, (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (cas: 209798-48-1Reference of 209798-48-1).

(2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (cas: 209798-48-1) 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. Reference of 209798-48-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

One-Pot Synthesis of Enantiopure Spiro[3,4-dihydrobenzo[b][1,4]oxazine-2,3′-oxindole] via Regio- and Stereoselective Tandem Ring Opening/Cyclization of Spiroaziridine Oxindoles with Bromophenols was written by Hajra, Saumen;Hazra, Atanu;Abu Saleh, S. K.. And the article was included in Journal of Organic Chemistry in 2019.Application of 6602-33-1 This article mentions the following:

A highly efficient regio- and stereoselective spiroaziridine ring opening with 2-bromophenols and a subsequent tandem cyclization reaction was developed for the one-pot synthesis of enantiopure 3,4-dihydrospiro[benzo[b][1,4]oxazine-2,3′-oxindole] with excellent enantiopurity (ee up to >99%). It is further extended to asym. synthesis of NH-free 3,4-dihydrospiro[benzo[b][1,4]oxazine-2,3′-oxindole] retaining the optical activity. In the experiment, the researchers used many compounds, for example, 2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1Application of 6602-33-1).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A comparative study of certain sulfisoxazole synthetic methods was written by Oeriu, S.;Voinescu, M.;Lupu, E.;Gloter, E.. And the article was included in Studii si Cercetari de Chimie in 1957.Synthetic Route of C12H8N4O This article mentions the following:

The 3 methods indicated (loc. cit.) for the synthesis of α-acetylpropionitrile, which on cyclization yielded dimethylaminoisoxazole were compared as were also the diverse variations for coupling the amine with p-acetamidobenzenesulfonyl chloride, and hydrolyzing the product. (11 references). In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Synthetic Route of C12H8N4O).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electrochemical studies and semiempirical calculations on π-conjugated dienones and heterocyclic nitrogen containing donor ligand molecules was written by Vatsadze, S.;Al-Anber, M.;Thiel, W. R.;Lang, H.;Holze, R.. And the article was included in Journal of Solid State Electrochemistry in 2005.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole This article mentions the following:

Reduction potentials for the first electron transfer to a broad selection of nitrogen containing bi- and polydentate mols. considered as potential ligands have been determined Results are compared with data obtained with semiempirical and UV-Vis spectroscopic data. Close correlations for the investigated mols. are observed Systematic differences in properties of mols. with and without the keto moiety can be explained by invoking MO and surface interaction arguments. Similar structural arguments can be used to explain the behavior of 2,4,6-tripyridin-2-yl[1,3,5]triazine. UV-Vis data match closely those derived from HOMO-LUMO calculations for these mols. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) 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 groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Developing Comprehensive Computational Parameter Sets To Describe the Performance of Pyridine-Oxazoline and Related Ligands was written by Guo, Jing-Yao;Minko, Yury;Santiago, Celine B.;Sigman, Matthew S.. And the article was included in ACS Catalysis in 2017.Application In Synthesis of (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole This article mentions the following:

The applicability of computational descriptors extracted from metal pyridine-oxazoline complexes to relate both site and enantioselectivity to structural diversity was investigated. A group of computationally derived features (e.g., metal NBO charges, steric descriptors, torsion angles) were acquired for a library of pyridine-oxazoline ligands. Correlation studies were employed to examine steric/electronic features described by each descriptor, followed by application of the said descriptors in modeling the results of two reaction types, the site-selective redox-relay Heck reaction and the enantioselective Carroll rearrangement, affording simple, well-validated models. Through exptl. validation and extrapolation, parameters derived from ground state metal complexes were found to be advantageous over those from the free ligand. In the experiment, the researchers used many compounds, for example, (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole (cas: 1257527-14-2Application In Synthesis of (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole).

(S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole (cas: 1257527-14-2) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application In Synthesis of (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

¹³C NMR spectra of 2,4-dihalopicolines and their N-oxides and IR spectra of 2-halopicoline N-oxides, 2,4-dihalopicoline N-oxides and 2-halo-4-nitropicoline N-oxides was written by Puszko, A.. And the article was included in Polish Journal of Chemistry in 1992.Formula: C6H5Br2N This article mentions the following:

The ¹³C NMR and IR spectra of the title compounds were recorded and their spectral parameters assigned. The influence of electronic properties of the substituents on the direction of chem. shifts and ν_N-O values is discussed. The ratio between a substituted heterocyclic compound and its parent and the identically substituted benzene derivatives has been determined In the experiment, the researchers used many compounds, for example, 2,4-Dibromo-5-methylpyridine (cas: 79055-50-8Formula: C6H5Br2N).

2,4-Dibromo-5-methylpyridine (cas: 79055-50-8) 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. 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.Formula: C6H5Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Design, Synthesis, and Fungicidal Activities of Novel Piperidyl Thiazole Derivatives Containing Oxime Ether or Oxime Ester Moieties was written by Bian, Qiang;Zhao, Rui-Qi;Peng, Xing-Jie;Gao, Li-Jie;Zhou, Guo-Na;Yu, Shu-Jing;Zhao, Wei-Guang. And the article was included in Journal of Agricultural and Food Chemistry in 2021.Synthetic Route of C11H20N2O2S This article mentions the following:

To explore the influence of the positions of the two nitrogen atoms on the thiazole ring and the isoxazoline ring on the activity, a series of novel piperidyl thiazole derivatives containing oxime ether and oxime ester moieties with two nitrogen atoms on the same or opposite sides have been designed, synthesized, and first evaluated for their fungicidal activities against Phytophthora capsiciin vitro. The bioassay results showed that the target compounds possessed moderate to good fungicidal activities against P. capsici, among which oxime ether compound I shows the highest fungicidal activity in vitro (EC₅₀ = 0.0104μg/mL) which is higher than dimethomorph (EC₅₀ = 0.1148μg/mL) and diacetylenyl amide (EC₅₀ = 0.040μg/mL). Compared with oxime ether compounds (the two nitrogen atoms are on the opposite sides), the activities of oxime ester compounds were significantly reduced. It is different from the com. fungicide fluoxapiprolin, and the activities of the compounds with the two nitrogen atoms on the same side were significantly reduced compared to the compounds with the two nitrogen atoms on the opposite sides. Moreover, some compounds showed moderate to good antifungal activities in vivo against Phytophthora capsici, Pseudoperonospora cubensis, and Phytophthora infestans. SEM of compound I on the hyphae morphol. showed that compound I might cause mycelial abnormalities of P. capsici. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (cas: 214834-18-1Synthetic Route of C11H20N2O2S).

tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (cas: 214834-18-1) 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.Synthetic Route of C11H20N2O2S

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Indolizine synthesis via copper-catalyzed cyclization of gem-difluoroalkenes and 2-(pyridin-2-yl)acetate derivatives was written by Lu, Chuan-Jun;Yu, Xin;Chen, Yu-Ting;Song, Qing-Bao;Wang, Hong. And the article was included in Organic Chemistry Frontiers in 2020.Application of 917023-06-4 This article mentions the following:

A novel and versatile approach to construct substituted indolizines I (R = H, 6-Br; Ar = Ph, 3,4-dimethoxyphenyl, thiophen-2-yl, (3E)-4-phenylbut-3-en-1-yl, etc.) through copper-catalyzed coupling cyclization of 2-(pyridin-2-yl)acetate II (R¹ = C(O)OMe, C(O)OEt, C(O)Oi-Pr, C(O)Me) with gem-difluoroalkenes ArCH=C(F)₂ has been developed. This method takes advantage of the cleavage of C-F bonds, providing a straightforward and efficient access to a variety of bisubstituted indolizine derivatives I in moderate to good yields with brilliant functional group compatibility. In the experiment, the researchers used many compounds, for example, Methyl 2-(5-bromopyridin-2-yl)acetate (cas: 917023-06-4Application of 917023-06-4).

Methyl 2-(5-bromopyridin-2-yl)acetate (cas: 917023-06-4) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Application of 917023-06-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem