Fused polyaza-heterocycles and 1,3,4-thiadiazoles via a tricyano synthon
✍ Scribed by Kamal M. Dawood; Mohamed A. Raslan
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2008
- Tongue
- English
- Weight
- 330 KB
- Volume
- 45
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
magnified image
Treatment of 2‐cyano‐3‐phenyl‐2‐pentenedinitrile with some heterocyclic diazonium salts afforded the corresponding heterocyclic hydrazones. Some of the latter hydrazones were converted into fused polyaza‐heterocycles upon boiling in pyridine. Reaction of 2‐cyano‐3‐phenyl‐2‐pentenedinitrile with phenylisothiocyanate gave a tricyano‐thiole derivative which on treatment with hydrazonoyl chlorides and 1‐(benzothiazol‐2‐yl)‐2‐bromoethanone furnished 1,3,4‐thiadiazole and thiazole derivatives, respectively.
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## Abstract magnified image The title compound 2‐butyl‐5‐chloro‐3__H__‐imidazole‐4‐carbaldehyde was transformed into tricyclic heterocycles by substituting the chlorine atom by an unsaturated thiolate or alkoxide and then converting aldehyde function into 1,3‐dipole. Chloramine‐T was used as an ef