Synthesis of 2-substituted pyridines from pyridine N-oxides

Liu, Chunli; Luo, Jiang; Xu, Lingli; Huo, Zhibao

doi:10.3998/ark.5550190.0014.105

Cited by 31 publications

(17 citation statements)

References 8 publications

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“…Biocatalysis is a useful supplementary technology for the chemical industry in the reactions that are not easily conducted in the organic chemistry methods 1 7 . For example, the reactions involved in the formation of 2-substituted pyridines and their derivatives from pyridine N -oxides are useful synthetic methods; however, these methods require strict conditions for high product yields 9 10 . In microorganisms, the pyridine 2-hydroxylation step is specifically catalyzed by a molybdenum-containing protein, such as nicotinic acid dehydrogenase (EC1.17.1.5) in nicotinic degradation pathway, and nicotine hydroxylase (EC1.5.99.4) and Spm ( Figure 2a ) in nicotine degradation pathways 11 12 .…”

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confidence: 99%

Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst

Tang

2014

Sci Rep

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Value-added intermediates produced by microorganisms during the catabolism of N-heterocycles are potential building blocks for agrochemical synthesis and pharmaceutical production. 6-Hydroxy-3-succinoyl-pyridine (HSP), an intermediate in nicotine degradation, is an important precursor for the synthesis of drugs and compounds with biological activities. In the present study, we show that an engineered biocatalyst, Pseudomonas putida P-HSP, efficiently produced HSP from the renewable raw material of tobacco-waste that contains a high concentration of nicotine. The genetically constructed strain P-HSP realized a high accumulation of HSP, and HSP production was 3.7-fold higher than the non-engineered strain S16. Under optimal conditions, HSP was produced at high concentrations of 6.8 g l−1 and 16.3 g l−1 from tobacco-waste and nicotine, respectively. This work demonstrates a green strategy to block the catabolic pathway of N-heterocycles, which is a promising approach for the mutasynthesis of valuable compounds.

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confidence: 99%

Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst

Tang

2014

Sci Rep

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“…2-Aminopyridine is synthesized by the reaction of pyridine with sodium amide (Chichibabin amination) [12]. It is obtained in high yield after the hydrolysis of the intermediate salt [13,14]. The reaction is shown below (figure 2).…”

Section: Figure 1 Drug Molecular Structures With Aminopyridine Consti...mentioning

confidence: 99%

“…3-aminopyridine is used as an intermediate for agrochemicals, pharmaceuticals and colourants [13,15], and is also listed as a plant growth regulator [16]. Derivatives of 3-aminopyridine are used as luminescent and liquid crystal materials as well as in photosensitizer and metal complex chemistry.…”

Section: -Aminopyridinementioning

confidence: 99%

Syntheses, Complexation and Biological Activity of Aminopyridines: A Mini-Review

Orie¹,

Duru²,

Ngochindo³

2021

AJHC

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Aminopyridines are among the classes of heterocyclic compounds that have been extensively studied in the last few decades owing to their interesting biological activities. They exist in three isomeric forms: 2-aminopyridine, 3-aminopyridine and 4-aminopyridine. The diversity in their pharmacological activities has attracted the attention of many researchers to explore the reasons for their wide potential. This study examines recent advances related to the efficient procedure for synthesizing different types of aminopyridine derivatives, its coordination site with metals and biological activities using systematic literature review and content analysis. Other important concepts of aminopyridines discussed are basicity, electric hindrance as related to percentage yield of isomeric forms and spectra updates on the characterization of aminopyridines. The findings from this study also reveal the array of solvents used for purification processes; ideas on isomers that have not been used in the synthesis of aminopyridine derivatives and their respective biological activities. The significance of this study is on the various synthetic methods revealed, which may be helpful to the development of newer compounds with aminopyridines moieties that could offer high bioactivity and lesser toxicity.

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“…Pyridine- N -oxides preactivated with acylating agents are ideal substrates in the reactions with a broad range of nucleophiles offering a valuable synthetic alternative to the nucleophilic substitution in 2-halopyridines and transition-metal-catalyzed reactions. − Nucleophilic displacement in 2-halopyridines is the strongly substrate-dependent reaction and typically requires harsh conditions, resulting in limited substrate scope and low functional group tolerance. To the contrary, addition of a nucleophile to an activated pyridine- N -oxide (generally prepared in situ) and the subsequent deoxygenative aromatization usually proceed efficiently under mild conditions, which improves functional group tolerance and overall applicability of the process.…”

Section: Introductionmentioning

confidence: 99%

Quaternary N-(2-Pyridyl)-DABCO Salts: One-Pot in Situ Formation from Pyridine-N-oxides and Reactions with Nucleophiles: A Mild and Selective Route to Substituted N-(2-Pyridyl)-N′-ethylpiperazines

2017

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The N-(2-pyridyl)-N'-ethylpiperazines are important structural motifs in several medicinally relevant compounds. Known synthetic methods toward these structures are multistep and generally based on the SAr-chemistry; their applicability is significantly limited to substrates containing electron-withdrawing groups. Here, we describe a new methodology for a rapid and modular access to this privileged scaffold. Importantly, the developed protocol proved to be very general and efficient for the substrates containing substituents of different electronic nature. An operationally simple, metal-free, one-pot synthetic procedure involves the initial reaction of activated heterocyclic N-oxides with DABCO, followed by in situ treatment of the resultant quaternary N-(2-pyridyl)-DABCO salts with nucleophiles, resulting in ring-opening. The method features mild reaction conditions, high positional selectivity, and excellent functional-group tolerance. The utility of our approach is demonstrated by the late-stage site-selective functionalizations of complex molecules; a rapid modular assembly of MC2050, a potent PARP-1 inhibitor; and gram-scale preparations.

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Synthesis of 2-substituted pyridines from pyridine N-oxides

Cited by 31 publications

References 8 publications

Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst

Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst

Syntheses, Complexation and Biological Activity of Aminopyridines: A Mini-Review

Quaternary N-(2-Pyridyl)-DABCO Salts: One-Pot in Situ Formation from Pyridine-N-oxides and Reactions with Nucleophiles: A Mild and Selective Route to Substituted N-(2-Pyridyl)-N′-ethylpiperazines

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