Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones.

doi:10.1021/acs.orglett.5b01241

Paper

Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones.

Published Jun 2, 2015 · Qinghe Gao, Shan Liu, Xia Wu

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87

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Abstract

A new strategy for the synthesis of 1,3,4-oxadiazoles was established through direct annulation of hydrazides with methyl ketones. It was found that the use of K2CO3 as a base achieves an unexpected and highly efficient C-C bond cleavage. This reaction is proposed to go through oxidative cleavage of Csp(3)-H bonds, followed by cyclization and deacylation.

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Study Snapshot

This study demonstrates a new strategy for synthesizing 1,3,4-oxadiazoles by directly annulating hydrazides with methyl ketones, using K2CO3 as a base and achieving efficient C-C bond cleavage.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones.

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References

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This study developed a novel method for synthesis of -ketoesters using TEMP and copper cocatalyzed oxidative coupling of methyl ketones with alcohols, offering a practical tool for late-stage modification of bioactive compounds.

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This study presents a metal-free synthesis of 1,3,4-oxadiazoles from N′-(arylmethyl)hydrazides or 1-(arylmethyl)-2-(arylmethylene)hydrazines, enabling the preparation of various 2,5-disubstituted

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Copper-catalyzed aerobic oxidative esterification of acetophenones with alcohols produces a broad range of -ketoesters in good yields, with carbonyl oxygen mainly originating from dioxygen.

Citations

I2-Mediated Synthesis of 1,3,4-Oxa/thiadiazoles from Aroylhydrazide and Acetonitrile/Thioacetamide.

I2-mediated oxidative amination of acetonitrile and aroyl hydrazide leads to the facile and efficient synthesis of 1,3,4-oxadiazoles with 50-82% yields.

Recent Development on the Heterocycles Derived From In Situ Formation of Aryl Glyoxals by Iodine/DMSO Mediated Oxidation of Methyl Ketones

The Iodine/DMSO system efficiently allows in situ formation of aryl glyoxals, enabling selective C-I and C-O bond formation and heterocycle synthesis in synthetic and medicinal chemistry.

I2-promoted one-pot synthesis of 1,3,4-oxadiazoles from aroyl hydrazides and methyl / ethyl acetate

This study successfully synthesized diverse 1,3,4-oxadiazoles using an I2-promoted one-pot method, achieving good to excellent yields and utilizing atomic economy principles.

Synthesis of pyrazole and 1,3,4-oxadiazole derivatives of pharmaceutical potential

This study presents an efficient and economical synthetic route for N-phenyl substituted pyrazole and 1,3,4-oxadiazole derivatives, which show potential as antituberculosis, anticonvulsant, antidiabetic, anticancer, and tyrosinas

2,5-Disubstituted structures of 1,3,4-oxadiazole and 1,3,4-thiodiazole for anti-inflammatory potential: DFT approach for the structural aspects

This study presents a efficient method for synthesizing 1,3,4-oxadiazole derivatives with promising anti-inflammatory and anti-diabetic properties using environmentally friendly solvents and microwave irradiation.