Synthesis of Two Isomeric Thiadiazine and Thiazole Derivatives from a Hydrazonoyl Halide

Thiadiazine and thiazoles have attracted importance due to their broad applicability as biologically active compounds. New thiadiazines and thiazoles are prepared via the simple reaction of an α-haloketohydrazonoyl with thiocarbohydrazone derivatives in a basic medium under reflux. A S-alkylated int...

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Bibliographic Details
Published in:Polycyclic aromatic compounds 2022-09, Vol.42 (8), p.5196-5203
Main Authors: Al-Faiyz, Yasair S., Sayed, Abdelwahed R.
Format: Article
Language:English
Subjects:
Alkylation
Bioactive compounds
Biological activity
Carbonyl compounds
Carbonyls
Hydrazonoyl
Nucleophiles
Reagents
Substitution reactions
thiadiazine
thiazole
Thiazoles
thiocarbohydrazone
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Summary:Thiadiazine and thiazoles have attracted importance due to their broad applicability as biologically active compounds. New thiadiazines and thiazoles are prepared via the simple reaction of an α-haloketohydrazonoyl with thiocarbohydrazone derivatives in a basic medium under reflux. A S-alkylated intermediate forms through nucleophile substitution involving the hydrazonoyl halogen and thiocarbohydrazone thiol. In situ cyclization via the condensation between the carbonyl and NH 2 or NH moieties of the intermediate forms 1,3,4-thiadiazine and thiazole derivatives, respectively. This method employs inexpensive, commercially available reagents and facile reaction conditions to afford novel thiadiazine/thiazole derivatives in good yields.
ISSN:1040-6638
1563-5333
DOI:10.1080/10406638.2021.1936085