An efficient synthesis of substituted 4-aryl-3-cyano-2-amino thiophenes by a stepwise Gewald reaction

TUMER F., Ekinci D., ZILBEYAZ K., DEMIR U.

TURKISH JOURNAL OF CHEMISTRY, cilt.28, sa.4, ss.395-403, 2004 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 28 Sayı: 4
  • Basım Tarihi: 2004
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.395-403
  • Anahtar Kelimeler: aminothiophenes, bromocrotonitriles, substituted aminothiophenes, ELECTROCHEMICAL OXIDATION, 2-AMINO-3-CYANO-4-PHENYLTHIOPHENE
  • Atatürk Üniversitesi Adresli: Evet

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.