Improved synthesis of 2,3-disubstituted pyridines by metallation of 2-chloropyridine: a convenient route to fused polyheterocycles

doi:10.1039/P19900002409

Paper

Improved synthesis of 2,3-disubstituted pyridines by metallation of 2-chloropyridine: a convenient route to fused polyheterocycles

Published 1990 · F. Trécourt, F. Marsais, T. Güngör

Journal of The Chemical Society-perkin Transactions 1

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38

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Abstract

Chemoselective directed metallation of 2-chloropyridine allows the synthesis of 2-substituted 3-carbonylated pyridines, advantage being taken of the metallation ortho-directing effect of the halogen, as well as its reactivity towards nucleophiles. Thus (2-chloro-, 2-methoxy-, and 2-amino-3-pyridyl)-ethanones and -arylmethanones as well as carbaldehydes have been prepared. Some of these ortho-disubstituted intermediates have been readily cyclized to fused polyheterocycles such as naphthyridines and aza-analogues of coumarins, xanthones, and acridones.

Study Snapshot

Directed metallation of 2-chloropyridine allows the synthesis of 2,3-disubstituted pyridines, which can be readily cyclized to fused polyheterocycles like naphthyridines and aza-analogues of coumarins,

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Improved synthesis of 2,3-disubstituted pyridines by metallation of 2-chloropyridine: a convenient route to fused polyheterocycles

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References

Metallation regioselective en serie pyridinique: Synthese originale d'amino-2 aroyl-3 pyridines

This study presents a regioselective metalation of 2-fluoropyridine with lithium diisopropylamide, leading to the synthesis of fluorinated alcohols and various 3-oxoalkyl- or 3-aroyl-2-aminopyridines.

Directed lithiation of 4-halopyridines: Chemoselectivity, regioselectivity and application to synthesis

Directed lithiation of 4-halopyridines allows for versatile functionalization and synthesis of various 3,4-disubstituted pyridines, with potential applications in nucleophilic chemistry.

Review on the metallation of π -deficient heteroaromatic compounds

3-fluoropyridine metallation at low temperatures using butyllithium-polyamine chelates or lithium diisopropylamide is chemoselective, allowing for the selective production of 2,3- or 3,4-disubstituted pyridines.

Pyridinethiones—V : Spectroscopic investigation and electronic structure of 3-formyl-2(1H)-pyridones, -thiones and -selones

The electronic build-up of 3-formyl-2(1H)-pyridones, -thiones, and -selones can be correlated with their chemical behavior through the perturbation model for chemical reactivity.

Benzopyranopyridine derivatives. 1. Aminoalkyl derivatives of the azaxanthenes as bronchodilating agents.

The 1-methyl-4-piperidylidene derivative of 1-azaxanthene shows potential as an oral effective potent bronchodilating agent and moderate antihistamine.

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