Butenolide annelation using a manganese(III) oxidation. A synthesis of 4-arylfuran-2(5H)-ones


Demir A. , Camkerten N., Gercek Z., Duygu N., Reis O., Arikan E.

TETRAHEDRON, cilt.55, ss.2441-2448, 1999 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 55 Konu: 8
  • Basım Tarihi: 1999
  • Doi Numarası: 10.1016/s0040-4020(99)00036-8
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.2441-2448

Özet

A general procedure was developed for the annelation of a butenolide to an aromatic ketone that highlighted a manganese(III) oxidation of aromatic ketones. The oxidation of aromatic ketones with manganese(III) acetate in the presence of 2;bromoacetic acid or the Mn(II) salt of this carboxylic acid provided a regioselectively convenient synthesis of 2-(2-bromoacetoxy) ketones. An Arbuzov or Wittig reaction of 2-(2-bromoacetoxy) ketones followed by cyclisation furnished 4-arylfuran-2(5H)-ones in good yield. (C) 1999 Elsevier Science Ltd. Ail rights reserved.