6533b7d2fe1ef96bd125f474

RESEARCH PRODUCT

ChemInform Abstract: Substituent Effect on Oxidative Cyclization of Aldehyde Thiosemicarbazones with Ferric Chloride.

Francesco BuccheriMichelangelo GruttadauriaGiuseppe CusmanoGiuseppe WerberRenato Noto

subject

chemistry.chemical_classificationReaction mechanismSubstituentGeneral MedicineRing (chemistry)AldehydeMedicinal chemistryChloridechemistry.chemical_compoundchemistrymedicineFerricOrganic chemistryPhenyl groupReactivity (chemistry)medicine.drug

description

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.

https://doi.org/10.1002/chin.199204075