Tag: 100-200

Regioselective C-H chlorination: towards the sequential difunctionalization of phenol derivatives and late-stage chlorination of bioactive compounds was written by Gao, Chao;Li, Hongchen;Liu, Miaochang;Ding, Jinchang;Huang, Xiaobo;Wu, Huayue;Gao, Wenxia;Wu, Ge. And the article was included in RSC Advances in 2017.COA of Formula: C11H9NO This article mentions the following:

A protocol for the auxillary directed C-H chlorination of phenol derivatives using catalytic amounts of palladium acetate that is amenable to the late-stage chlorination of diflufenican and estrone was developed. The 2-pyridine group allows for a highly efficient palladium-catalyzed chlorination and sequential ortho C-H functionalization reaction of phenol derivatives to produce a variety of sym. and unsym. 2,4,6-trisubstituted phenols. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0COA of Formula: C11H9NO).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol� in pyridine vs. 150 kJ·mol� 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.COA of Formula: C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reaction of aromatic N-oxides with dipolarophiles. XI. 1,3-Dipolar cycloaddition reaction of pyridine N-oxides with tosyl isocyanate and one-pot synthesis of 2-oxooxazolo[4,5-b]pyridine derivatives was written by Hisano, Takuzo;Harano, Kazunobu;Fukuoka, Ryuichi;Matsuoka, Toshikazu;Muraoka, Keiji;Shinohara, Ikuo. And the article was included in Chemical & Pharmaceutical Bulletin in 1986.Application In Synthesis of 3,5-Dimethylpyridine 1-oxide This article mentions the following:

The cycloaddition reactivity of 4-MeC₆H₂SO₂NCO toward pyridine N-oxides was calculated by the CNDO/2 method using a perturbation equation, and the results indicated that the initial stage of the reaction might be controlled by coulombic attraction. The 1,3-dipolar cycloaddition reaction of 4-MeC₆H₄SO₂NCO with 2 equivalent of 3,5-dibromopyridine N-oxide in refluxing C₆H₆ gave 6-bromo-2-oxooxazolo[4,5-b]pyridine, whereas the use of 1 equivalent of 3,5-dichloropyridine N-oxide gave 6,7a-dichloro-2-oxo-3-tosyl-3a,7a-dihydrooxazolo[4,5-b]pyridine, formed from the 1,5-sigmatropic rearrangement of the primary cycloadduct. When the reaction was carried out in the presence of Et₃N in C₆H₆ 6-halo-2-oxo-3-tosyloxazolo[4,5-d]pyridine was isolated. The observed activation parameters, as well as the small solvent effects, may be interpreted in terms of a concerted pathway. The reaction should be very valuable as a one-pot synthesis of 2-oxooxazolo[4,5-b]pyridines, which are pyridine analogs of 5-chloro-2-benzoxazolinone. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Application In Synthesis of 3,5-Dimethylpyridine 1-oxide).

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. 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. Application In Synthesis of 3,5-Dimethylpyridine 1-oxide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Metal-Free Ortho C-H Borylation of 2-Phenoxypyridines under Mild Conditions was written by Niu, Liting;Yang, Haijun;Wang, Ruji;Fu, Hua. And the article was included in Organic Letters in 2012.Name: 2-Phenoxypyridine This article mentions the following:

An efficient metal-free ortho C-H borylation has been developed via sequential borylation of substituted 2-phenoxypyridines with BBr₃ following esterification with pinacol. The corresponding aryl boronates were obtained in good yields. The synthesized aryl boronates can be easily transformed into various useful products. Therefore, the present method makes functionalizations of aryl C-H bonds easy. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Name: 2-Phenoxypyridine).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol� in pyridine vs. 150 kJ·mol� in benzene). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Name: 2-Phenoxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A Three-Step Synthesis of Acotiamide for the Treatment of Patients with Functional Dyspepsia was written by Fu, Kai;Yang, Liu;Wang, Qiu-Fen;Zhan, Fu-Xu;Wang, Bin;Yang, Qian;Ma, Zhi-Jia;Zheng, Geng-Xiu. And the article was included in Organic Process Research & Development in 2015.Electric Literature of C5H6ClN This article mentions the following:

A three-step synthesis of acotiamide is described. The agent is marketed in Japan for treatment of patients with functional dyspepsia. We designed a one-pot method to prepare the key intermediate I from 2,4,5-trimethoxybenzoic acid via an acyl chloride and amide and then reacted with H₂NCH₂CH₂N(iPr)₂ to obtain acotiamide under solvent-free condition. With the use of DCC, an unavoidable impurity was also successfully converted into the desired acotiamide. After isolation of acotiamide, we carried forward to the next step of HCl salt formation, which proved to be a very effective procedure for the removal of practically all major impurities. The process is cost-effective, simple to operate, and easy to scale-up. 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 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 derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Electric Literature of C5H6ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Nitrogen reduction and functionalization by a multimetallic uranium nitride complex was written by Falcone, Marta;Chatelain, Lucile;Scopelliti, Rosario;Zivkovic, Ivica;Mazzanti, Marinella. And the article was included in Nature (London, United Kingdom) in 2017.Category: pyridine-derivatives This article mentions the following:

Mol. nitrogen (N₂) is cheap and widely available, but its unreactive nature is a challenge when attempting to functionalize it under mild conditions with other widely available substrates (such as carbon monoxide, CO) to produce value-added compounds Biol. N₂ fixation can do this, but the industrial Haber-Bosch process for ammonia production operates under harsh conditions (450 °C and 300 bar), even though both processes are thought to involve multimetallic catalytic sites. And although mol. complexes capable of binding and even reducing N₂ under mild conditions are known, with co-operativity between metal centers considered crucial for the N₂ reduction step, the multimetallic species involved are usually not well defined, and further transformation of N₂-binding complexes to achieve N-H or N-C bond formation is rare. Haber noted, before an iron-based catalyst was adopted for the industrial Haber-Bosch process, that uranium and uranium nitride materials are very effective heterogeneous catalysts for ammonia production from N₂. However, few examples of uranium complexes binding N₂ are known, and soluble uranium complexes capable of transforming N₂ into ammonia or organonitrogen compounds have not yet been identified. Here we report the four-electron reduction of N₂ under ambient conditions by a fully characterized complex with two U(III) ions and three K⁺ centers held together by a nitride group and a flexible metalloligand framework. The addition of H₂ and/or protons, or CO to the resulting N2(4-) complex results in the complete cleavage of N₂ with concomitant N₂ functionalization through N-H or N-C bond-forming reactions. These observations establish that a mol. uranium complex can promote the stoichiometric transformation of N₂ into NH₃ or cyanate, and that a flexible, electron-rich, multimetallic, nitride-bridged core unit is a promising starting point for the design of mol. complexes capable of cleaving and functionalizing N₂ under mild conditions. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Category: pyridine-derivatives).

Pyridinehydrochloride (cas: 628-13-7) 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.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Nitrogen bridgehead compounds. Part 5. Cyclization of 2-(2-pyridylaminomethylene)-succinates and -glutarates was written by Vasvari-Debreczy, Lelle;Hermecz, Istvan;Meszaros, Zoltan;Horvath, Agnes;Simon-Parkanyi, Piroska. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1978.Category: pyridine-derivatives This article mentions the following:

Cyclization of succinates I (n = 1, R = H, alkyl, OH, Cl, NO₂, NHCOMe, CONH₂) gave 40-92% pyrido[1,2-a]pyrimidines and pyridylpyrrolinones. The latter may form pyridylpyrroles by reaction with POCl₃. The ratio of pyridopyrimidines to pyridylpyrroles was dependent upon the nature and position of the pyridine ring substituent. Substituents at position 6 hindered pyridopyrimidine formation whereas those at position 3 inhibited the formation of pyridylpyrrolinones. Only pyrido[1,2-a]pyrimidines were formed from the cyclization of the homologous glutarates I (n = 2). In the experiment, the researchers used many compounds, for example, N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3Category: pyridine-derivatives).

N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3) 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. Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Selective Metalation and Functionalization of Fluorinated Nitriles Using 2,2,6,6-Tetramethylpiperidyl Bases was written by dos Santos, Thiago;Orenha, Henrique P.;Murie, Valter E.;Vessecchi, Ricardo;Clososki, Giuliano C.. And the article was included in Organic Letters in 2021.Electric Literature of C6H3FN2 This article mentions the following:

Herein, regioselective deprotometalation of aromatic and heteroaromatic nitriles has been accomplished using (TMP)₂Zn·2MgCl₂·2LiCl and TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidinyl) with the exploration of new and scarcely investigated metalation positions. Regioselectivity was rationalized by DFT calculations The quenching of the generated organozinc and organomagnesium intermediates with various electrophiles gave access to 47 highly functionalized nitriles with yields up to 95%. Addnl., a difunctionalization strategy and the use of functionalized nitriles as building blocks to construct relevant heterocycles have been reported. In the experiment, the researchers used many compounds, for example, 2-Fluoroisonicotinonitrile (cas: 3939-14-8Electric Literature of C6H3FN2).

2-Fluoroisonicotinonitrile (cas: 3939-14-8) 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. Electric Literature of C6H3FN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electrochemical fluorosulfonylation of alkenes to access vicinal fluorinated sulfones derivatives was written by Zhao, Bin;Pan, Zichen;Zhu, Anqiao;Yue, Yanni;Ma, Mengtao;Xue, Fei. And the article was included in Tetrahedron in 2022.Recommanded Product: Phenyl(pyridin-2-yl)methanone This article mentions the following:

Herein, a practical and efficient fluorosulfonylation of the various alkenes with sulfonyl radical sources and Et₃N·3HF as cost-effective fluorination reagents under mild conditions is reported. Remarkably, this protocol features very green and sustainable conditions obviating the need of chem. oxidants and transition metal catalyst. A variety of substituents on both sulfonyl hydrazides and alkenes are tolerated to give vicinal fluorinated sulfones in moderate to excellent yields. Also, the synthetic utility of this transformation is further demonstrated by a gram-scale reaction and the late-stage functionalization of complex mols. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Recommanded Product: Phenyl(pyridin-2-yl)methanone).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) 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. 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: Phenyl(pyridin-2-yl)methanone

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Studies on new reactions of pyridine-copper chloride complex was written by Zeng, Xian-Mou;Chen, Xi-Wen;Xu, Ren-Xian;Sun, Yun-Song;Yu, Shu-Wen;Guo, Lian-Ying;Cheng, Guo-Bao;Gu, Yi-Jian. And the article was included in Scientia Sinica (English Edition) in 1981.Reference of 644-98-4 This article mentions the following:

Cu(py)₂Cl₂ undergoes alkylation at the γ- and α-positions of the pyridine ligands upon reaction with alkyl halides in the presence of Na under mild conditions. The products are decomposed by alkali to give the α- and γ-alkylpyridines in <40% yields. The γ-alkylpyridines are the main products. 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’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.Reference of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of 2- and 4-cyanopyridines was written by Okamoto, Toshihiko;Tani, Hideo. And the article was included in Chem. & Pharm. Bull. (Tokyo) in 1959.SDS of cas: 1620-76-4 This article mentions the following:

Addition of MeI or Me₂SO₄ to pyridine or quinoline N-oxides gave their quaternary salts, which were stirred 1 hr. at room temperature with KCN to give 2- and 4-cyano derivatives of pyridine or quinoline, separated by extraction with CHCl₃ and either vacuum distillation or Al₂O₃ chromatography of the extract The compound whose N-oxide was used, % yield, m.p. (or b.p.), and m.p. of the picrate of its 4-cyano derivative, and the same data repeated for its 2-cyano derivative were: C₅H₅N, 25, 78-80°, 197-9°, 50, b₂₀ 110-17°, -; 2-picoline, 18, -, 164-5°, (6-cyano derivative) 45, 70-2°, -; 3-picoline, 15, -, 154-6°, 30, 85-6°, -; 4-picoline, 28, 88-91° -, -, -, -; 2,6-lutidine, 13, 80-3°, 175-8°, (6-cyanomethyl-2-picoline) 33, b₂₂ 125-33°, 176-9°; and quinoline, trace, -, 175-7°, 70, 91-5°, -. All products were identified by mixed m.p. with samples synthesized by different routes. The ratio of isomers formed depended on reaction conditions. Two mechanisms were suggested for the reaction. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4SDS of cas: 1620-76-4).

4-Methylpicolinonitrile (cas: 1620-76-4) 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 groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.SDS of cas: 1620-76-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem