6533b7d9fe1ef96bd126c3c5

RESEARCH PRODUCT

A quantitative study of substituent effects on oxidative cyclization of some 2-methylsubstituted aldehydes. Thiosemicarbazones induced by ferric chloride

Renato NotoGiuseppe WerberPaolo Lo MeoMichelangelo Gruttadauria

subject

Oxidative cyclizationChemistryOrganic ChemistrySubstituentChlorideMedicinal chemistryMetalchemistry.chemical_compoundvisual_artOxidizing agentvisual_art.visual_art_mediummedicineFerricmedicine.drug

description

In order to gain further mechanistical information about the cyclization of thiosemicarbazones and thiosemicarbazone-type substrates induced by metallic salts as oxidizing agents, we performed the synthesis of substrates 1a-s and a kinetic study of the oxidative cyclization of 1 to 5-imino-Δ2-1,3,4-thiadiazole 2 and 1,2,4-triazoline-5-thione 3 derivatives induced by methanolic ferric chloride solutions. The results of cyclization were compared to those of corresponding semicarbazones. The kinetic data were analyzed by means of the Hammett's equation and ρ values discussed.

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