A chemo- and regiocontrolled approach to bipyrazoles and pyridones via the reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with hydrazines.

doi:10.1039/c7ob02725g

Paper

A chemo- and regiocontrolled approach to bipyrazoles and pyridones via the reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with hydrazines.

Published Mar 7, 2018 · D. Obydennov, L. R. Khammatova, O. S. Eltsov

Organic & biomolecular chemistry

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Abstract

Chemo- and regiocontrolled syntheses of pyrazoles and pyridones are presented on the basis of 4-pyrones. A novel approach towards highly functionalized 3,4'-bipyrazoles has been developed by using reactions of ethyl 5-acylcomanoates with hydrazines. The acid-promoted double cyclocondensation allows switching of the structure of the pyrazole rings easily through changing both the nature of hydrazine and the reaction conditions. The transformation of 4-pyrones with phenylhydrazine in EtOH at -20 °C leads to hydroxypyridones as monoaddition products which can be used as precursors for the preparation of pyridone and pyrazole derivatives. A novel rearrangement of 2-hydroxypyridone to pyrazolyl-1,3-diketones in DMSO was found. The structure and regiochemistry of bipyrazoles were confirmed by X-ray analysis and 2D NMR experiments.

Study Snapshot

This study presents a novel chemo- and regiocontrolled approach to synthesize bipyrazoles and pyridones using ethyl 5-acylcomanoates with hydrazines, enabling the easy switching of pyrazole ring structures and pyridone

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

A chemo- and regiocontrolled approach to bipyrazoles and pyridones via the reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with hydrazines.

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References

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Ethyl 4-(5-arylisoxazol-4-yl)-2,4-dioxobutanoates can be synthesized from ethyl 5-aroyl-4-pyrone-2-carboxylates and hydroxylamine in ethanol at -20

Citations

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

This study presents a convenient approach to substituted pyrazoles and pyridazinones based on 1,2,4-triketones, revealing chemo- and regioselective transformations and the potential of acetyl and carbethoxy groups as building blocks for

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