Regioselective Synthesis of the 5,6-Dihydro-4H-furo[2,3-c]pyrrol-4-one Skeleton: A New Class of Compounds

Koza G., Karahan E., BALCI M.

HELVETICA CHIMICA ACTA, vol.93, no.9, pp.1698-1704, 2010 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 93 Issue: 9
  • Publication Date: 2010
  • Doi Number: 10.1002/hlca.200900448
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1698-1704
  • Middle East Technical University Affiliated: Yes

Abstract

We hereby report the first preparation of the 5,6-dihydro-4H-furo[2.3-c]pyrrol-4-one (3) and its derivatives starting from methyl 3-(methoxycarbonyl)furnan-2-acetate (8). The ester functionality connected to the methylene group was regiospecifically converted to the desired monohydrazide 9. Conversion of 9 into the acyl azide In followed by Curtius rearrangement gave the corresponding isocyanate derivative 11 (Scheme 2). Reaction of 11 with different nucleophiles produced urethane and urea derivatives (Scheme 3). Intramolecular cyclization reactions provided the target compounds (Scheme 5). Removal of the amine-protecting group formed the title compound 3.