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Substituent effect on oxidative cyclization of aldehyde thiosemicarbazones with ferric chloride
Author(s) -
Noto Renato,
Buccheri Francesco,
Cusmano Giuseppe,
Gruttadauria Michelangelo,
Werber Giuseppe
Publication year - 1991
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.5570280539
Subject(s) - chemistry , aldehyde , substituent , ferric , reactivity (psychology) , ring (chemistry) , nitrogen atom , chloride , medicinal chemistry , nitrogen , organic chemistry , catalysis , medicine , alternative medicine , pathology
The reactivity of aldehyde thiosemicarbazones 1 with ferric chloride solutions was examined. When compounds 1 are not substituted on the N‐2 nitrogen atom formation of 1,3,4‐thiadiazole 3 heterocyclic ring was observed. In contrast 1,2,4‐triazoline 4 and/or 1,3,4‐thiadiazoline 5 heterocyclic rings were afforded when N‐2 nitrogen atom carried a methyl or a phenyl group. The reaction mechanism is also discussed.