An effective new synthesis of 2-aminopyrrole-4-carboxylates

Demir A., Emrullahoglu M.

TETRAHEDRON, cilt.61, sa.44, ss.10482-10489, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 61 Sayı: 44
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.tet.2005.08.050
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.10482-10489
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Efficient syntheses of 2-aminopyrroles are presented starting from beta-dicarbonyl compounds, bromoacetonitrile, and amines. Alkylation of beta-dicarbonyl compounds with bromoacetonitrile furnished alpha-cyanomethyl-beta-dicarbonyl compounds. The condensation reaction of alpha-cyanomethyl-beta-dicarbonyl compounds with amines catalyzed by p-TsOH affords the corresponding enamines in good yields. Base catalyzed cyclization via the addition of an amine moiety to the carbon-nitrogen triple bond of nitrile furnished 2-aminopyrroles in high yields. (c) 2005 Elsevier Ltd. All rights reserved.