Selective one-pot synthesis of substituted pyrrole-3-phosphonates from alpha-cyanomethyl-beta-ketoesters

Demir A. S. , Tural S.

TETRAHEDRON, cilt.63, sa.19, ss.4156-4161, 2007 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 63 Konu: 19
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.tet.2007.02.097
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.4156-4161


A one-step synthesis of 5-alkoxypyrrole-3-phosphonates is presented starting from suitable alpha-cyanomethyl-beta-ketophosphonates. The key step in the synthesis involves a one-pot addition and heteroannulation sequence. The zinc perchlorate-catalyzed addition of alcohols to the nitrile carbon of alpha-cyanomethyl- beta-ketophosphonates followed by annulation furnished 5-alkoxypyrrole-3-phosphonates. The addition-annulation process is carried out in the presence of water and 4,5-dihydro-5-oxo-1H-pyrrole-3-phosphonates (pyrrolinones) are obtained in good yields. (C) 2007 Elsevier Ltd. All rights reserved.