A study of the mechanism of the oxidative cyclization of benzaldehyde semicarbazones induced by cupric perchlorate in acetonitrile

6533b839fe1ef96bd12a6e18

RESEARCH PRODUCT

A study of the mechanism of the oxidative cyclization of benzaldehyde semicarbazones induced by cupric perchlorate in acetonitrile

Paolo Lo Meo Renato Noto Vincenzo Frenna Michelangelo Gruttadauria Giuseppe Werber

subject

Reaction rate Benzaldehyde Oxidative cyclization Perchlorate chemistry.chemical_compound Reaction rate constant Chemistry Organic Chemistry Nitro Organic chemistry Reactivity (chemistry)Acetonitrile Medicinal chemistry

description

Treatment of benzaldehyde semicarbazones 1a-i with cupric perchlorate in acetonitrile at 40 provided selectively the corresponding 1,2,4-triazolin-5-ones 2a-i. The relative rate constants for 2a-i formation were determined by the competitive method. The results obtained showed that electron-donating substituents (methyl and methoxy) increase the reaction rate, while the reverse was found for electron-withdrawing substituents (chloro and nitro group). The reactivity data are discussed on the grounds of two possible mechanisms.

year	journal	country	edition	language
1995-07-01	Journal of Heterocyclic Chemistry

https://doi.org/10.1002/jhet.5570320430

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