Dergiler / Turkish Journal of Chemistry / 2004 / Cilt: 28 - Sayı: 4
An Efficient Synthesis of Substituted 4-Aryl-3-Cyano-2-Amino Thiophenes by a Stepwise Gewald Reaction
- Sayfa
- 395–404
- DOI
- —
Özet
The title compounds were efficiently synthesised starting from aryl methyl ketones in 3 steps. Knoevenagel condensation of aryl methyl ketones with malononitrile gave the corresponding crotonitriles (5a-f). Methyl groups of the crotonitriles (5a-f) were then efficiently brominated by refluxing and lightening the reaction media to give bromocrotonitriles (6a-f). The bromocrotonitriles (6a-f) were finally cyclised by treatment with NaSH to give the title compounds.
Abstract
The title compounds were efficiently synthesised starting from aryl methyl ketones in 3 steps. Knoevenagel condensation of aryl methyl ketones with malononitrile gave the corresponding crotonitriles (5a-f). Methyl groups of the crotonitriles (5a-f) were then efficiently brominated by refluxing and lightening the reaction media to give bromocrotonitriles (6a-f). The bromocrotonitriles (6a-f) were finally cyclised by treatment with NaSH to give the title compounds.