Studies on the Vilsmeier-haack reaction. Part XIII: Novel heterocyclo-substituted 4,4′-bi-pyrazolyl dithiocarbamate derivatives
✍ Scribed by Ibrahim M. A. Awad
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 2007
- Tongue
- English
- Weight
- 469 KB
- Volume
- 56
- Category
- Article
- ISSN
- 0268-2575
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✦ Synopsis
Abstract
5‐Imino‐3‐methyl‐l‐phenyl‐2‐pyrazoline‐4‐dithiocarbamic acid (I) underwent simultaneous formylation and dimerization reactions with the Vilsmeier reagent giving 4‐[5′‐imino‐3‐(1″‐formyl‐2″‐dimethylaminoethenyl)‐3′‐methyl‐1′‐phenyl‐1′H‐pyrazolo‐4′‐dithiocarbamyl‐2,4‐dihydro‐3‐imino‐5‐methyl‐2‐phenyl‐1‐pyrazoline]dithiocarbamate (II) which hydrolysed with sodium hydroxide to give 4‐[3′‐(1″‐formyl‐2″‐hydroxyethenyl)‐3′‐methyl‐1‐phenyl‐1′‐H‐pyrazolo‐4′‐dithiocarbamyl‐1′‐pyrazoline]dithiocarbamate‐5,5′‐dione (IV). Treatment of II and/or IV with morpholine, piperidine, piperazine, hydroxylamine, hydrazine hydrate or phenylhydrazine afforded the corresponding dipyrazolo‐4,4′‐dithiocarbamate derivatives with different heterocyclic systems at the 3‐position. The structures of these compounds were confirmed by microanalysis data, IR and ^1^H‐NMR spectrometry. All synthesized compounds have been screened in vitro against Gram‐positive and Gram‐negative bacteria, and fungi.