Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations

Hommes, Paul; Reißig, Hans‐Ulrich

doi:10.3762/bjoc.12.112

Cited by 14 publications

(4 citation statements)

References 60 publications

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“…7.0 and ca. 6.0, respectively]; − (ii) relatively good solubility in aqueous media (e.g., 5.9 mg/mL in water); (iii) potential applications in the brain (e.g., intraperitoneally administered bpy was able to prevent and reduce intracerebral hemorrhage in vivo); (iv) ease of structural transformations . In addition, previous studies of bpy reported its ability to regulate metal-mediated reactions in biological systems [e.g., reducing the formation of hydrogen peroxide triggered by Fe(II/III)], , supporting its applicability in biology.…”

Section: Resultsmentioning

confidence: 96%

Strategic Design of 2,2′-Bipyridine Derivatives to Modulate Metal–Amyloid-β Aggregation

Ji¹,

Lee²,

Kim³

et al. 2017

Inorg. Chem.

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The complexity of Alzheimer's disease (AD) stems from the inter-relation of multiple pathological factors upon initiation and progression of the disease. To identify the involvement of metal-bound amyloid-β (metal-Aβ) aggregation in AD pathology, among the pathogenic features found in the AD-affected brain, small molecules as chemical tools capable of controlling metal-Aβ aggregation were developed. Herein, we report a new class of 2,2'-bipyridine (bpy) derivatives (1-4) rationally designed to be chemical modulators toward metal-Aβ aggregation over metal-free Aβ analogue. The bpy derivatives were constructed through a rational design strategy employing straightforward structural variations onto the backbone of a metal chelator, bpy: (i) incorporation of an Aβ interacting moiety; (ii) introduction of a methyl group at different positions. The newly prepared bpy derivatives were observed to bind to metal ions [i.e., Cu(II) and Zn(II)] and interact with metal-Aβ over metal-free Aβ to varying degrees. Distinguishable from bpy, the bpy derivatives (1-3) were indicated to noticeably modulate the aggregation pathways of Cu(II)-Aβ and Zn(II)-Aβ over metal-free Aβ. Overall, our studies of the bpy derivatives demonstrate that the alteration of metal binding properties as well as the installation of an Aβ interacting capability onto a metal chelating framework, devised via the rational structure-based design, were able to achieve evident modulating reactivity against metal-Aβ aggregation. Obviating the need for complicated structures, our design approach, presented in this work, could be appropriately utilized for inventing small molecules as chemical tools for studying desired metal-related targets in biological systems.

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Section: Resultsmentioning

confidence: 96%

Strategic Design of 2,2′-Bipyridine Derivatives to Modulate Metal–Amyloid-β Aggregation

Ji¹,

Lee²,

Kim³

et al. 2017

Inorg. Chem.

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“…DCPFC was synthesized by the literature 53 and 2-(Pyridin-2-yl)Pyridine was described 54 . Methane Carboxylic acid was purified by the standard procedure and the fraction distilling at 118 o C was collected 55 2,6-DicarboxyPyridinium Fluoro chromate (DCPFC) is easily prepared by the reaction of pyridine-2,6-dicarboxylic acid with chromium trioxide in HF 53…”

Section: Methodsmentioning

confidence: 99%

Catalytic Oxidation of 2-Amino-3-Sulfhydryl Propanoic Acid (ASPA) by 2,6- Dicarboxypyridinium Fluorochromate (DCPFC) : A Kinetic and Mechanistic Study

Mohanapriya

Dharmaraja²,

Raj

et al. 2022

Int J Life Sci Pharm Res

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2-(Pyridin-2-yl) pyridine catalyzed oxidation of 2-amino-3-sulfhydryl propanoic acid (ASPA) by 2,6-DicarboxyPyridinium Fluoro Chromate (DCPFC) has been carried out at 308 K. This amino acid oxidation leads to the formation of a product. Main objective of our present investigation is, Kinetic Oxidation reaction is carried out, from this, reaction rate law, rate equation, mechanisms and rate constant values were measured. Various factors such as Oxidant, Substrate, Acid, Solvent, Catalyst, MnSO4, Acrylonitrile, and NaClO4 influence the reaction rate. This kind of systematic kinetic work explores the physical characterization of the reacting Species. This catalyzed reaction exhibits first order dependence, with respect to [DCPFC] and fractional order with respect to [ASPA], [H+] and 2-(pyridin-2-yl)pyridine. The above reaction is carried out at methane carboxylic acid-water medium. Rate of the reaction has been influenced by varying the percentage of methane carboxylic acid. Addition of NaClO4 appreciably decreases the rate of the reaction. Addition of acrylonitrile does not influence the rate of the reactions, which rules out the polymerization reaction indicating the lack of a free radical pathway. Slight increase in the rate values occur by the addition of MnSO4, which implies that, slight catalytic behaviour of Mn2+ on Oxidation reaction. The reaction described above was carried out at four different temperatures to determine, thermodynamic parameters such as enthalpy and entropy of activation. The appropriate mechanism has been suggested based on the observed data. Our Aim is to find out the reaction mechanism pathway, Order of the reaction by means of various effects such as Oxidant effect, Solvent & Catalyst Effect, etc.,. The product analysis has been confirmed by IR spectral studies and derivative test.

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“…In particular, these compounds can be obtained from 2,2’‐bipyridines via nucleophilic substitution of hydrogen by the reaction of methyllithium with the following oxidative aromatization of the σ H ‐adduct or by using cross‐coupling reactions . Additionally, various types of heterocyclization reactions were carried out, e . g .…”

Section: Methodsmentioning

confidence: 99%

Direct Introduction of a Methyl Group at the C5‐Position of 1,2,4‐Triazines: Convenient Synthesis of 6‐Functionalized 5‐Aryl‐2,2′‐bipyridines

et al. 2020

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This article describes a convenient method for the synthesis of 5‐aryl‐6‐methyl‐2,2′‐bipyridines through the direct introduction of a methyl group at the C5‐position of 1,2,4‐triazine moieties. At first 1,2,4‐triazine precursors are synthesized for this purpose. The reaction proceeds through SNH/SNips° substitution and subsequent aza‐Diels‐Alder reaction. In addition, mono‐ and dibromomethyl‐substituted 2,2’‐bipyridines are also synthesized to confirm the applicability of the present method.

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Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations

Cited by 14 publications

References 60 publications

Strategic Design of 2,2′-Bipyridine Derivatives to Modulate Metal–Amyloid-β Aggregation

Strategic Design of 2,2′-Bipyridine Derivatives to Modulate Metal–Amyloid-β Aggregation

Catalytic Oxidation of 2-Amino-3-Sulfhydryl Propanoic Acid (ASPA) by 2,6- Dicarboxypyridinium Fluorochromate (DCPFC) : A Kinetic and Mechanistic Study

Direct Introduction of a Methyl Group at the C5‐Position of 1,2,4‐Triazines: Convenient Synthesis of 6‐Functionalized 5‐Aryl‐2,2′‐bipyridines

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