ipso-Substitution of a sulphinyl or sulphonyl group attached to pyridine rings and its application for the synthesis of macrocycles

doi:10.1039/P19840001839

Paper

ipso-Substitution of a sulphinyl or sulphonyl group attached to pyridine rings and its application for the synthesis of macrocycles

Published 1984 · N. Furukawa, S. Ogawa, T. Kawai

Journal of The Chemical Society-perkin Transactions 1

UNKNOWN SJR score

20

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0

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Abstract

A sulphinyl or sulphonyl group directly bound to the 2- or 4-position of a pyridine ring was readily displaced by several nucleophiles such as RO–, RS–, and CN– to afford the corresponding ipso-substitution products. Similarly, 2-halogeno-6-methylsulphinyl- or -methylsulphonyl-pyridines also react with nucleophiles to afford 2-halogeno-6-substituted pyridine derivatives. Thus, the leaving abilities of the leaving groups fall in the order RSO2 > RSO > Br ≃ Cl RS (R = alkyl or benzyl). The ipso-substitution can be applied to the synthesis of 2,6-disubstituted pyridino macrocycles containing both carbon–oxygen and carbon–sulphur bridges, resulting in several new macrocycles in moderate yields.

Study Snapshot

This study demonstrates that ipso-substitution of sulphinyl or sulphonyl groups on pyridine rings can be applied to the synthesis of 2,6-disubstituted pyridino macrocycles with moderate yields.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

ipso-Substitution of a sulphinyl or sulphonyl group attached to pyridine rings and its application for the synthesis of macrocycles

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References

Citations

Transition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond

This study successfully achieved transition-metal-free cross-coupling of aryl(heteroaryl) methyl sulfoxides and alcohols to afford alkyl aryl(heteroaryl) ethers, offering potential for medicinal chemistry applications.

Formal Bimolecular [2 + 2 + 2] Cycloaddition Strategy for the Synthesis of Pyridines: Intramolecular Propargylic Ene Reaction/Aza Diels-Alder Reaction Cascades.

This study presents two strategies for the synthesis of multisubstituted pyridines using intramolecular propargylic ene reactions and aza Diels-Alder reaction cascades, providing versatile intermediates for oxygen and carbon nucleophile substitution reactions.

4-Aminopyrimidine libraries from the Ugi-Smiles reaction of thiouracil

The Ugi-Smiles reaction of thiouracil efficiently prepares diverse aminopyrimidine libraries in one-pot procedures, demonstrating its efficiency and efficiency in one-pot procedures.

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