Studies on the Regioselective Nucleophilic Aromatic Substitution (SNAr) Reaction of 2-Substituted 3,5-Dichloropyrazines

2013 ◽  
Vol 15 (9) ◽  
pp. 2156-2159 ◽  
Author(s):  
Stephanie Scales ◽  
Sarah Johnson ◽  
Qiyue Hu ◽  
Quyen-Quyen Do ◽  
Paul Richardson ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Snar Reaction

scholarly journals N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine

Molbank ◽  
10.3390/m1030 ◽  
2018 ◽  
Vol 2018 (4) ◽  
pp. M1030 ◽  
Author(s):  
Dhafer Zinad ◽  
Dunya AL-Duhaidahaw ◽  
Ahmed Al-Amiery ◽  
Abdul Kadhum
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
High Performance ◽  
Nucleophilic Aromatic Substitution ◽  
Gas Chromatography Mass Spectrometry ◽  
Aromatic Substitution ◽  
Target Compound ◽  
Chromatography Mass Spectrometry ◽  
Snar Reaction ◽  
Layer Chromatography

N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized by chemical analysis, which includes nuclear magnetic resonance (NMR) (1H-NMR and 13C-NMR), Thin Layer Chromatography-Mass Spectrometry (TLC-MS), high- performance liquid chromatography (HPLC), Gas Chromatography-Mass Spectrometry (GC-MS), and elemental analysis.

Highly Regioselective DABCO-Catalyzed Nucleophilic Aromatic Substitution (SNAr) Reaction of Methyl 2,6-Dichloronicotinate with Phenols.

ChemInform ◽  
2006 ◽  
Vol 37 (25) ◽  
Author(s):  
Yao-Jun Shi ◽  
Guy Humphrey ◽  
Peter E. Maligres ◽  
Robert A. Reamer ◽  
J. Michael Williams
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Snar Reaction

Uncatalyzed CO2Li-Mediated SNAr Reaction of Unprotected Benzoic Acids via Silicon Trickery

2016 ◽  
Vol 69 (3) ◽  
pp. 307 ◽  
Author(s):  
Mickael Belaud-Rotureau ◽  
Anne-Sophie Castanet ◽  
Thi Huu Nguyen ◽  
Jacques Mortier
Keyword(s):  
Methoxy Group ◽  
Intermediate Formation ◽  
Coupling Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Direct Access ◽  
Nucleophilic Attack ◽  
Benzoic Acids ◽  
Aromatic Substitution ◽  
Snar Reaction ◽  
Ketone Formation

The alkyl and aryllithium nucleophilic aromatic substitution (SNAr) displacement of a fluoro or methoxy group from unprotected 2-fluoro/methoxybenzoic acids is discussed. It was discovered that a TMS group located at the C6-position ortho to the carboxyl group shields effectively the carboxylate against nucleophilic attack, thus reducing dramatically ketone formation, and reorients nucleophilic substitution to the C2-position. The reactions with fluoro-substituted substrate 7 proceed efficiently; in contrast, the use of methoxy-functionalized benzoic acid 8 only affords moderate yields with s-BuLi and PhLi. This uncatalyzed coupling reaction, which provides a direct access to biaryl compounds, presumably proceeds by an addition–elimination sequence via intermediate formation of a resonance-stabilized pentavalent silalactone-Meisenheimer complex.

One-Pot Approach for SNAr Reaction of Fluoroaromatic Compounds with Cyclopropanol

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 982-986
Author(s):  
Hao Jin ◽  
Zhuo Gao ◽  
Shaodong Zhou ◽  
Chao Qian
Keyword(s):  
Aromatic Compounds ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
One Pot ◽  
Mild Conditions ◽  
Snar Reaction ◽  
Novel Method ◽  
The One ◽  
Application Scope

A novel method for preparing aromatic compounds containing cyclopropoxy via nucleophilic aromatic substitution reaction (SNAr) of fluoroaromatic compounds with cyclopropanol under relatively mild conditions is presented. As compared to the approaches reported previously for preparing 1-(cyclopropyloxy)-2-nitrobenzene, the one proposed in this work is simplified without sacrificing the yields: When the reaction was performed at 75 °C with Cs2CO3 as the base and DMF as solvent, after 6 h the yield was up to 90%. Finally, various fluoroaromatic compounds were employed as substrates for a test that proves a wide application scope of the method.

scholarly journals Nucleophilic Aromatic Substitution of Polyfluoroarene to Access Highly Functionalized 10-Phenylphenothiazine Derivatives

2021 ◽  
Author(s):  
Kotaro Kikushima ◽  
Haruka Koyama ◽  
Kazuki Kodama ◽  
Toshifumi Dohi
Keyword(s):  
Aromatic Compounds ◽  
Nucleophilic Aromatic Substitution ◽  
Free Access ◽  
Aromatic Substitution ◽  
Halogen Bonds ◽  
Metal Free ◽  
Potential Applicability ◽  
Selective Substitution ◽  
Snar Reaction

Nucleophilic aromatic substitution (SNAr) reactions can provide metal-free access to synthesize mono-substituted aromatic compounds. We have developed efficient SNAr conditions for p-selective substitution of polyfluoroarenes with phenothiazine in the presence of a mild base to afford the corresponding 10-phenylphenothiazine (PTH) derivatives. The resulting polyfluoroarene-bearing PTH derivatives were subjected to a second SNAr reaction to generate highly functionalized PTH derivatives with potential applicability as photocatalysts for the reduction of carbon–halogen bonds.

scholarly journals Synthesis of α- and β-Carbolines by a Metalation/Negishi Cross-Coupling/SNAr Reaction Sequence

2021 ◽  
Author(s):  
Shainthavaan Sathiyalingam ◽  
Stefan Roesner
Keyword(s):  
Efficient Method ◽  
Continuous Flow ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Reaction Sequence ◽  
Snar Reaction ◽  
Privileged Scaffolds

Carbolines are considered to be privileged scaffolds in medicinal chemistry. An efficient method for the synthesis of α- and β-carbolines from fluoropyridines and 2-haloanilines is reported. This streamlined procedure consists of a four-step directed ortho-lithiation, zincation, Negishi cross-coupling, and intramolecular nucleophilic aromatic substitution, providing access to a diverse set of functionalized carbolines. While the procedure is applicable to batch conditions, the generation of arylzinc intermediates in continuous flow has been demonstrated.

Micellar catalysis of organic reactions. IX. The reaction of sodium azide with activated aromatic halides and the subsequent decomposition of the initially formed aryl azide

1982 ◽  
Vol 35 (12) ◽  
pp. 2557 ◽  
Author(s):  
TJ Broxton ◽  
AC Jakovljevic
Keyword(s):  
Sodium Azide ◽  
Substitution Reaction ◽  
Cetyltrimethylammonium Bromide ◽  
Micellar Catalysis ◽  
Organic Reactions ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Aryl Azide ◽  
Snar Reaction ◽  
Subsequent Decomposition

The effect of micelles of cetyltrimethylammonium bromide on the SNAr reaction of azide ions with 1-halogeno-2,4-dinitrobenzenes and on the subsequent decomposition of the aryl azide product has been measured. The nucleophilic aromatic substitution reaction is shown to be subject to significant micellar catalysis whereas the subsequent decomposition of the aryl azide is not.

One-pot Microwave-assisted Tandem Deprotection of Arylmethanesulfonates / SNAr Reaction for K2CO3-mediated C(Aryl)–O Bond Formation

2007 ◽  
Vol 62 (9) ◽  
pp. 1183-1186 ◽  
Author(s):  
Hui Xu ◽  
Hong-Feng Li
Keyword(s):  
Substitution Reaction ◽  
Bond Formation ◽  
Aryl Halides ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
One Pot ◽  
Diaryl Ethers ◽  
Microwave Assisted ◽  
Snar Reaction

One-pot microwave-assisted tandem deprotection of arylmethanesulfonates / nucleophilic aromatic substitution reaction (SNAr) with activated aryl halides to synthesize asymmetrical diaryl ethers is described.

Dynamics of a gas-phase SNAr reaction: non-concerted mechanism despite the Meisenheimer complex being a transition state

2020 ◽  
Vol 22 (45) ◽  
pp. 26562-26567
Author(s):  
Nishant Sharma ◽  
Rupayan Biswas ◽  
Upakarasamy Lourderaj
Keyword(s):  
Transition State ◽  
Gas Phase ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Concerted Mechanism ◽  
Snar Reaction

Multi-step roaming pathway in the nucleophilic aromatic substitution reaction involving a Meisenheimer transition state.

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