Synthesis of 6-Chloro-5-(trifluoroacetyl)pyridine-3-carbonitrile: A Novel, Versatile Intermediate for the Synthesis of Trifluoromethylated Azaindazole Derivatives

Channapur, Manjunath B.; Hall, Roger G.; Kessabi, Jilali; Montgomery, Mark; Shyadligeri, A. S.

doi:10.1055/s-0037-1611815

Cited by 3 publications

(1 citation statement)

References 9 publications

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“…Hydrazinylpyridines and their substituted analogues are simple organic molecules that can be used for many further transformations: acting as nucleophiles, [2][3][4][5] for the synthesis of more complex nitrogen heterocyclic compounds, mainly various [1,2,3]triazolopyridines [5][6][7] and azaindazoles, 8 or for hydrazone formation. 5 Hydrazine and its substituted analogues can be furthermore used for the synthesis of pyrazole and its derivatives.…”

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Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[2.2.2]octenes Fused with Two N-Aminosuccinimide Moieties

Ekar¹,

Kranjc²

2020

Synthesis

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Efficient and reliable synthesis of substituted hydrazinylpyridines in thick-wall ACE tubes via nucleophilic substitution of a chlorine substituent in different chloropyridines is presented. Hydrazine hydrate and alkylhydrazines were used as nucleophiles and simple alcohols and diethyl ether were the only organic solvents necessary, making the process environmentally and user friendly, potentially reaching 100% atomic efficiency. In the next step, transformations of succinic anhydride moieties fused to the bicyclo[2.2.2]octene framework into succinimide moieties via nucleophilic substitution of oxygens were conducted. As nucleophiles two of the synthesized hydrazinylpyridines (2-hydrazinyl-3-nitropyridine and 2-hydrazinyl-5-nitropyridine) and also hydrazine hydrate, phenylhydrazine, and 4-nitrophenylhydrazine were used. Reactions were again carried out in ACE tubes and only simple alcohols, diethyl ether, and acetone were needed as solvents. One of the prepared bicyclo[2.2.2]octene adducts displayed water solubility thus being a promising candidate for future studies as a novel bidentate ligand for various metal cations in aqueous solutions or acting as an unprecedented halogen bond acceptor.

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Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[2.2.2]octenes Fused with Two N-Aminosuccinimide Moieties

Ekar¹,

Kranjc²

2020

Synthesis

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Synthesis of 2‐Chloro‐6‐(trifluoromethyl)pyridine‐3,5‐dicarbonitrile: A Versatile Building Block for the Synthesis of Substituted Trifluoro Methyl Pyridine Derivatives

Channapur¹,

Hall

Kessabi

et al. 2023

ChemistrySelect

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A simple and highly efficient (concise 3-step) synthesis of 2chloro-6-(trifluoromethyl)pyridine-3,5-dicarbonitrile has been developed from readily available starting materials. Furthermore, the selective reactivity of this tetra-substituted pyridine with different carbon, sulfur, nitrogen and oxygen nucleophiles offers great scope for the synthesis of novel highly substituted pyridine derivatives in decent to good yields.

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Five-membered ring systems: with more than one N atom

Yet

2021

Progress in Heterocyclic Chemistry

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Synthesis of 6-Chloro-5-(trifluoroacetyl)pyridine-3-carbonitrile: A Novel, Versatile Intermediate for the Synthesis of Trifluoromethylated Azaindazole Derivatives

Abstract: A synthesis of 6-chloro-5-(trifluoroacetyl)pyridine-3-carbonitrile, a versatile building block for the synthesis of trifluoromethylated N-heterocycles, is described. The reactions of 6-chloro-5-(trifluoroacetyl)pyridine-3-carbonitrile with 1,2- and 1,3-bisnucleophiles were investigated.

Cited by 3 publications

References 9 publications

Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[2.2.2]octenes Fused with Two N-Aminosuccinimide Moieties

Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[2.2.2]octenes Fused with Two N-Aminosuccinimide Moieties

Synthesis of 2‐Chloro‐6‐(trifluoromethyl)pyridine‐3,5‐dicarbonitrile: A Versatile Building Block for the Synthesis of Substituted Trifluoro Methyl Pyridine Derivatives

Five-membered ring systems: with more than one N atom

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