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, vol.55, no.8, pp.2441-2448, 1999 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 55 Issue: 8
  • Publication Date: 1999
  • Doi Number: 10.1016/s0040-4020(99)00036-8
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2441-2448
  • Middle East Technical University Affiliated: Yes

Abstract

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.