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A quantitative study of substituent effects on oxidative cyclization of some 2‐methylsubstituted aldehydes. Thiosemicarbazones induced by ferric chloride
Author(s) -
Noto Renato,
Meo Paolo Lo,
Gruttadauria Michelangelo,
Werber Giuseppe
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330353
Subject(s) - chemistry , ferric , substituent , oxidizing agent , chloride , semicarbazone , oxidative phosphorylation , medicinal chemistry , organic chemistry , biochemistry
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‐Δ 2 ‐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.