Synthesis of 2,5-Diaryltetrazoles from N-Phenylsulfonylbenzhydrazidoyl Chlorides and Arylhydrazines

doi:10.1246/BCSJ.49.762

Paper

Synthesis of 2,5-Diaryltetrazoles from N-Phenylsulfonylbenzhydrazidoyl Chlorides and Arylhydrazines

Published Mar 1, 1976 · S. Ito, Yumo Tanaka, A. Kakehi,

Bulletin of the Chemical Society of Japan

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38

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Abstract

A new synthesis of 2,5-diaryltetrazoles is given by the reaction of N-phenylsulfonylbenzhydrazidoyl chlorides with arylhydrazines and the action of potassium carbonate on the intermediate product formed in the initial reaction. Thirty tetrazoles carrying H, CH3, Cl, Br, or NO2 as the para-substituent of the 2-phenyl group, and H, CH3, Cl, CH3O, CN, or NO2 as that of the 5-phenyl group, were synthesized in 70–16% yields, respectively. The reaction may proceed via the concerted elimination of benzenesulfinate ion from the intermediate 1,3-diaryl-5-phenylsulfonylformazanide anion taking a quasi-aromatic configuration.

Study Snapshot

This study demonstrates a new synthesis of 2,5-diaryltetrazoles from N-phenylsulfonylbenzhydrazidoyl chlorides and arylhydrazines, with 70-16% yields, and suggests a quasi-aromatic

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of 2,5-Diaryltetrazoles from N-Phenylsulfonylbenzhydrazidoyl Chlorides and Arylhydrazines

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References

Reaction between p-Toluenesulfinic Acid and Diphenyldiazomethane

P-toluenesulfinic acid and diphenyldiazomethane react faster in non-polar solvents, with protonation of diphenyldiazomethane being the rate-determining step.

1.5-Dipolare Cyclisierungen, I. Begriffsbestimmung und Beiträge zur Imidazid/Tetrazol-Tautomerie

1.5-Dipolar Cyclization is a general method for synthesizing heterocycles, with new examples on imidazide/tetrazole tautomerism equilibrium.

The Dependence of Conformational and Isomer Stability on the Number of Electrons in Extended π Systems

The stability of conformational and isomer conformations in extended K systems is influenced by the number of electrons in extended K systems, with cis-methyl allyl anions being more stable than corresponding cations.

Citations

Metal-Free Regioselective N2-Arylation of 1H-Tetrazoles with Diaryliodonium Salts.

This study presents a metal-free regioselective N2-arylation strategy for synthesizing 2,5-diaryl-tetrazoles from nitriles, offering potential for biologically active molecules.

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Glucose-based 2-[18F]FBDG is a promising dual-probe for GLUT1 imaging in breast cancer, with potential for improved metabolic stability in vivo.

One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles

This one-pot Suzuki-hydrogenolysis protocol allows for the modular synthesis of 2,5-diaryltetrazoles, enabling a library of these compounds for photochemistry applications.

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Bu4NI-catalyzed regioselective N-methylation, N2-alkylation, and N2-arylation of tetrazoles using organic peroxides/peresters provides moderate to good yields and is amenable to a broad range of substrates.

Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry

Photoclick chemistry allows for triple orthogonal labeling of glycans, enabling the visualization of carbohydrates in living cells.