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.

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

Efficient Synthesis of 3,4-Disubstituted 7-Azaindoles Employing SEM as a Dual Protecting–Activating Group

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2273-2278 ◽  
Author(s):  
Piroska Gyárfás ◽  
János Gerencsér ◽  
Warren S. Wade ◽  
László Ürögdi ◽  
Zoltán Novák ◽  
...  
Keyword(s):  
Functional Groups ◽  
Efficient Method ◽  
Reaction Times ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Efficient Synthesis ◽  
Mild Conditions

An efficient method for nucleophilic aromatic substitution on 7-azaindoles has been developed. The reaction is facilitated by the unique dual influence of SEM as both protecting and activating group, permitting mild conditions and short reaction times that are compatible with sensitive functional groups. The method is suitable for the synthesis of a broad range of products, most notably ethers.

scholarly journals A Greener and Efficient Method for Nucleophilic Aromatic Substitution of Nitrogen-Containing Fused Heterocycles

Molecules ◽  
2018 ◽  
Vol 23 (3) ◽  
pp. 684 ◽  
Author(s):  
Joana Campos ◽  
Mohammed Loubidi ◽  
Marie-Christine Scherrmann ◽  
Sabine Berteina-Raboin
Keyword(s):  
Efficient Method ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Fused Heterocycles

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

Combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions as a versatile route to pyrimidines bearing thiophene fragments

Tetrahedron ◽  
2012 ◽  
Vol 68 (27-28) ◽  
pp. 5445-5452 ◽  
Author(s):  
Egor V. Verbitskiy ◽  
Ekaterina M. Cheprakova ◽  
Pavel A. Slepukhin ◽  
Mikhail I. Kodess ◽  
Marina A. Ezhikova ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

scholarly journals Icosahedral Meta-Carboranes Containing Exopolyhedral B-Se and B-Te Bonds

2021 ◽  
Author(s):  
Harrison Mills ◽  
Fadi Alsarhan ◽  
Ta-Chung Ong ◽  
Milan Gembicky ◽  
Arnold Rheingold ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Nucleophilic Aromatic Substitution ◽  
Grignard Reagents ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Reactivity Pattern ◽  
Electrophilic Reactions ◽  
Substitution Chemistry ◽  
Electrophilic Reactivity

Chalcogen-containing carboranes have been known for several decades and possess stable exopolyhedral B(9)-Se and B(9)-Te σ bonds despite the electron-donating ability of the B(9) vertex. While these molecules are known, little has been done to thoroughly evaluate their electrophilic and nucleophilic behavior. Herein, we report an assessment of the electrophilic reactivity of meta-carboranyl selenyl (II), tellurenyl (II), and tellurenyl (IV) chlorides and establish their reactivity pattern with Grignard reagents, alkenes, alkynes, enolates, and electron-rich arenes. These electrophilic reactions afford unique electron-rich B-Y-C (Y = Se, Te) bonding motifs not commonly found before. Furthermore, we show that meta-carboranyl selenolate, and even meta-carboranyl tellurolate, can be competent nucleophiles and participate in nucleophilic aromatic substitution reactions. Arene substitution chemistry is shown to be further extended to electron-rich species via the palladium mediated cross-coupling chemistry.

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